Synthesis of 5-aminosalicylic acid

Preparation of 5-aminosalicylic acid

Preparation of 5-aminosalicylic acid

Preparation of 5-aminosalicylic acid

A mixture of 50 g. of aniline hydrochloride, 60 g. of conc. hydrochloric acid, and 300 g. of ice is diazotized by adding a solution of 29 g. of sodium nitrite in 100 ml of water to the mixture. After 15 minutes the diazonium salt is run into a solution of 53.3 g. of salicylic acid in 220 g. of crystallized sodium carbonate and a liter of water. The sodium salt separates, is filtered and washed with a little water. The azo compound is next boiled with about a liter of water, sodium hydroxide solution added until alkaline and dry sodium hyposulphite (about 135 g.) added until the reduction is complete. After the aniline is removed by steam distillation, acid is added, and the free 5-aminosalicylic acid separates (m.p. 280 °C dec.).

Systematic organic chemistry, by W. M. Cumming, 365-366, 1937.

IUPAC Name

5-amino-2-hydroxybenzoic acid

InChI

InChI=1S/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)

InChI Key

KBOPZPXVLCULAV-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=C(C=C1N)C(=O)O)O

MeSH Synonyms

5 Aminosalicylate, 5 Aminosalicylic Acid, 5-Aminosalicylate, 5-Aminosalicylic Acid, Allphar Brand of Mesalamine, Antigen Brand of Mesalamine, Asacol, Asacolon, Ascolitin, Axcan Brand of Mesalamine, Byk Brand of Mesalamine, Canasa, Celltech Brand of Mesalamine, Claversal, Falk Brand of Mesalamine, Farmasa Brand of Mesalamine, Ferring Brand of Mesalamine, Fivasa, GlaxoSmithKline Brand of Mesalamine, Henning Berlin Brand of Mesalamine, Hydrochloride, Mesalamine, Lixacol, m Aminosalicylic Acid, m-Aminosalicylic Acid, Merckle Brand of Mesalamine, Mesalamine, Mesalamine Hydrochloride, Mesalamine Monosodium Salt, Mesalazine, Mesasal, meta Aminosalicylic Acid, meta-Aminosalicylic Acid, Monosodium Salt, Mesalamine, Norgine Brand of Mesalamine, Novo 5 ASA, Novo-5 ASA, Novo5 ASA, Novopharm Brand of Mesalamine, Pentasa, Procter and Gamble Brand of Mesalamine, Provalis Brand of Mesalamine, Rowasa, Salofalk, Sanofi Synthelabo Brand of Mesalamine, Schering Plough Brand of Mesalamine, Schering-Plough Brand of Mesalamine, SmithKline Brand of Mesalamine, Solvay Brand of Mesalamine, Yamanouchi Brand of Mesalamine

Depositor-Supplied Synonyms

5-Aminosalicylic acid, mesalamine, Mesalazine, 5-Amino-2-hydroxybenzoic acid, 89-57-6, Claversal, Salofalk, Asacol, Canasa, Pentasa, Rowasa, Mesasal, m-Aminosalicylic acid, 5-ASA, Fisalamine, Lialda, Lixacol, Asacolitin, Apriso, Benzoic acid, 5-amino-2-hydroxy-, 5-amino-2-hydroxy-benzoic acid, Asacol HD, 5-Aminosalicylate, p-Aminosalicylsaeure, Mesalazinum, Mesalazina, Mezavant, sfRowasa, 3-carboxy-4-hydroxyaniline, SALICYLIC ACID, 5-AMINO-, Mesalazinum [Latin], Mesalazina [Spanish], 2-Hydroxy-5-aminobenzoic acid, Mesavancol, 5-AS, Delzicol, Mesacol, Mesavance, Pentacol, Iialda, meta-Aminosalicylic Acid, 5-Amino Salicylic Acid, Mesalazine MMX, Mezavant XL, UNII-4Q81I59GXC, NSC 38877, Mesalamine (USP), Pentasa (TN), p-Aminosalicylsaeure [German], Salofalk Granu-Stix, Asacol (TN), Mesalamine [USAN], Rowasa (TN), CCRIS 7334, CHEBI:6775, MLS001424012, S1681_Selleck, Mesalazine (JAN/INN), AC1L1HCS, Prestwick0_001069, Prestwick1_001069, Prestwick2_001069, Prestwick3_001069, EINECS 201-919-1, MFCD00007877, WLN: ZR DQ CVQ, CHEMBL704, BRN 2090421, CAS-89-57-6, Oprea1_847633, A79809_ALDRICH, BSPBio_001058, KBioGR_002425, KBioSS_002431, SMR000145728, A3537_SIGMA, A6178_SIGMA, ARONIS23914, BIDD:GT0811, SPBio_002969, AI3-15564, MLS000758287, AC1Q51L9, BPBio1_001164, 5-Aminosalicylic Acid, Purified, 09409_FLUKA, 09410_FLUKA, 6291-36-7 (hydrochloride), HSDB 7512, KBio2_002425, KBio2_004993, KBio2_007561, KBio3_002904, AJG-501, cMAP_000045, MAX-002, SPD-476, SPD-480, KBOPZPXVLCULAV-UHFFFAOYSA-N, BB_NC-0015, HMS1571E20, HMS2051M21, HMS2090I09, NSC38877, STK301678, AKOS000118959, Mesalamine HCl, AC-2764, DB00244, LS-1894, MD-0901, NCGC00016344-01, NCGC00016344-03, NCGC00090934-01, NCGC00090934-02, CPD000145728, SAM001247020, 35589-28-7 (mono-hydrochloride salt), AB1001921, A0317, AB00374979, Z-206, DSSTox_CID_4506, D00377, DSSTox_RID_77435, DSSTox_GSID_24506, 4-14-00-02058 (Beilstein Handbook Reference), I06-0488, A3613/0153179, Asacolon, Ascolitin, Fivasa, 5-aminosalicylic acid, Mesalazine, Asacol, Pentasa, Canasa, Mesalamine, 5 Aminosalicylate, InChI=1/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11, 61513-32-4, Novo5 ASA, m Aminosalicylic Acid, 5 Aminosalicylic Acid, Novo 5 ASA, Novo-5 ASA, meta Aminosalicylic Acid, Byk Brand of Mesalamine, Falk Brand of Mesalamine, Hydrochloride, Mesalamine, Axcan Brand of Mesalamine, Mesalamine Monosodium Salt, Solvay Brand of Mesalamine, Allphar Brand of Mesalamine, Antigen Brand of Mesalamine, Farmasa Brand of Mesalamine, Ferring Brand of Mesalamine, Merckle Brand of Mesalamine, Monosodium Salt, Mesalamine, Norgine Brand of Mesalamine, mesalsal, Celltech Brand of Mesalamine, Provalis Brand of Mesalamine, Pentasareg, Salozinal, Asalit, Ipocol, Novopharm Brand of Mesalamine, Yamanouchi Brand of Mesalamine, SmithKline Brand of Mesalamine, Asacol|, Sf Rowasa, minosalicylic acid, CID4075, Mesalamine (TN), Henning Berlin Brand of Mesalamine, Delzicol (TN), Sfrowasa (TN), GlaxoSmithKline Brand of Mesalamine, Schering Plough Brand of Mesalamine, Schering-Plough Brand of Mesalamine, Pendo-5 Asa, 5-Aminosalicylicacid, Apriso (TN), Canasa (TN), Iialda (TN), Lialda (TN), Procter & Gamble Brand of Mesalamine, Sanofi Synthelabo Brand of Mesalamine, Teva-5 Asa, Asacol 800, 5-amino-salicylic acid, PubChem17623, Mesalamine|||Mesalazine, ACMC-1BKFR, Mesalamine [USAN:USP], Ntp-5-aminosalicylic Acid, Pentasa Suppository – 1g, Pentasa Enema 1g/100ml, Pentasa Enema 2g/100ml, Pentasa Enema 4g/100ml, cid_4075, D019804, SCHEMBL31297, 3amino-6-hydroxybenzoic acid, 5-amino-2-hydroxybenzoicacid, KSC448C0L, 3-amino-6-hydroxybenzoic acid, 4Q81I59GXC, GTPL2700, ZINC1688, DTXSID5024506, BDBM60918, CTK3E8105, HMS2098E20, HMS3393M21, HMS3649K15, Pharmakon1600-01505993, Salicylic acid, 5-amino- (8CI), ACN-S002469, Tox21_110384, Tox21_201610, Tox21_303125, 5-Amino-2-hydroxybenzoic acid 97%, AN-874, ANW-39326, BBL013046, DAP000729, FC1035, NSC-38877, NSC759301, SBB052617, Tox21_110384_1, BCP9000175, CCG-100829, CS-2219, CS-O-05654, CS-O-10279, CS16234, HS-0100, LS11426, MCULE-5752745805, NC00079, NSC-759301, RP21708, TRA0073805, Mesalamine-Supplied by Selleck Chemicals, Pentasa Extended-release Tablets 250mg, Pentasa Extended-release Tablets 500mg, NCGC00016344-02, NCGC00016344-04, NCGC00016344-05, NCGC00016344-07, NCGC00257142-01, NCGC00259159-01, AJ-08068, AK-72925, BP-13074, BR-72925, HY-15027, OR011141, OR174775, KB-196569, KB-196728, ST2411704, ST4109571, TR-032941, AM20060091, FT-0619950, Salofalk (r) 5-asa Suppositories – 250mg, 1764-EP2272825A2, 1764-EP2275420A1, M-7246, 24215-EP2289518A1, 24215-EP2295053A1, 24215-EP2295409A1, 24215-EP2314574A1, 24215-EP2314590A1, 90701-EP2371811A2, AB00374979-09, AB00374979-10, AB00374979_11, AB00374979_12, Salofalk (r) 5-asa Enteric Coated Tab- 250mg, Q-201355, T5894395, F1918-0003, 5-Amino-2-hydroxybenzoic acid; 5-AS; Mesalamine; 5-ASA

Removed Synonyms

||Asacolitin, Aminosalicylic acid, Mesalamine Hydrochloride, C7H7NO3, MolPort-001-641-024, RTR-032941, A2291, B1969, 35589-28-7, 6291-36-7, m-A

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