Synthesis of 4-amino-3-hydroxybenzoic acid

Preparation of 4-amino-3-hydroxybenzoic acid

Preparation of 4-amino-3-hydroxybenzoic acid

Preparation of 4-amino-3-hydroxybenzoic acid

10 g. 4-nitro-3-hydroxy benzoic acid and 200 ml conc. hydrochloric acid are heated on a water bath, and 30 g. of tin slowly added. After the reaction is complete the double tin salt separates out, and is filtered. The precipitate is dissolved in 200 ml of warm water and hydrogen sulfide passed until all the tin is separated. The filtrate from the tin is concentrated until crystals of the hydrochloride begin to separate. When cold, the hydrochloride is filtered, dissolved in a little water, and the free base precipitated by the addition of a conc. solution of sodium acetate. It is filtered, washed with water, and recrystallised from hot water or dilute alcohol. Yield 60% theoretical (5 g.), m.p. 115-116 ° C.

Systematic organic chemistry, by W. M. Cumming, 360, 1937.

IUPAC Name

4-amino-3-hydroxybenzoic acid

InChI

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

InChI Key

NFPYJDZQOKCYIE-UHFFFAOYSA-N

Canonical SMILES

C1=CC(=C(C=C1C(=O)O)O)N

MeSH Synonyms

4-amino-3-hydroxybenzoic acid

Depositor-Supplied Synonyms

4-Amino-3-hydroxybenzoic acid, 2374-03-0, 3-hydroxy-4-aminobenzoic acid, 4-Amino-3-hydroxy benzoic acid, MFCD00017094, CHEMBL1462, NFPYJDZQOKCYIE-UHFFFAOYSA-N, benzoic acid, 4-amino-3-hydroxy-, SBB052678, 2hdr, 3-hydroxy paba, PubChem14418, 3-hydroxy-4-amino acid, AC1L3AVI, 2-Amino-5-carboxyphenol, Intermediates-ZCF02635, ACMC-209g5k, 4-Carboxy-2-hydroxyaniline, AC1Q51YM, KSC202O8F, SCHEMBL180385, 339598_ALDRICH, AC1Q516E, 4-amino-3-hydroxy-benzoic acid, CTK1A2782, DTXSID90178409, Benzoicacid, 4-amino-3-hydroxy-, OTAVA-BB 1514172, KUC106686N, ZINC156556, STR04495, 4-amino-3-hydroxybenzoic acid 97%, 4-amino-3-hydroxybenzoic acid,98%, ANW-25206, BDBM50324681, GEO-00141, LABOTEST-BB LT00455247, NSC407243, AKOS005255334, AC-4479, AS00858, CM12417, CS20332, MCULE-1439462293, NSC-407243, PS-4562, RL02751, TRA0032503, AJ-13841, AK-34278, AN-11962, BC225276, BR-34278, EN002762, KB-36357, OR012665, R068, SY018797, KSC-11-207-17, AB0017973, ST2418097, TC-064139, 4CH-014273, AM20060231, FT-0617496, ST50824391, EN300-42793, M-3149, I01-5027, Q-200427, T7084681, 4-carboxy-2-hydroxyaniline, 2-amino-5-carboxyphenol, InChI=1/C7H7NO3/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,9H,8H2,(H,10,11, 4A3

Removed Synonyms

C7H7NO3, MolPort-001-767-512, CID137566, RTC-064139, A1194, 4-AMINO-1-METHYL-3-PROPYLPYRAZOLE-5-CARBOXAMIDE HYDROCHLORIDE

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