Synthesis of 5-amino-2-chlorobenzoic acid

Preparation of 5-amino-2-chlorobenzoic acid

Preparation of 5-amino-2-chlorobenzoic acid

Preparation of 5-amino-2-chlorobenzoic acid

20.2 grams (0.1 mole) of 2-chloro-5-nitrobenzoic acid are dissolved in 70 ml. water containing 5.5 grams of sodium carbonate. The solution is then acidified by the addition of 10 ml. 40 % acetic acid and is added dropwise to a boiling suspension of 100 grams of zinc dust in 250 ml. water to which 4 ml. 40 % acetic acid has been added. The mixture is boiled and stirred continuously, and since bad foaming is often encountered, a large reaction vessel should be used (3-liter enameled crock). The reduction takes about 2 hours, after which 5 grams of sodium carbonate is added and the solution is filtered. The filtrate is evaporated to 200 ml. 5-amino-2-chlorobenzoic acid is isolated by acidifying the solution with hydrochloric acid, avoiding an excess. The yield is about 92 %.

The fundamental processes of dye chemistry, by H. E. Fierz-David, 169, 1949

IUPAC Name

5-amino-2-chlorobenzoic acid

InChI

InChI=1S/C7H6ClNO2/c8-6-2-1-4(9)3-5(6)7(10)11/h1-3H,9H2,(H,10,11)

InChI Key

GVCFFVPEOLCYNN-UHFFFAOYSA-N

Canonical SMILES

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

Depositor-Supplied Synonyms

5-Amino-2-chlorobenzoic acid, 89-54-3, 2-Chloro-5-aminobenzoic acid, 3-amino-6-chlorobenzoic acid, 5-Amino-2-chloro-benzoic acid, Benzoic acid, 5-amino-2-chloro-, 3-carboxy-4-chloroaniline, 5-Amino-2-chlorobenzoicacid, 5-amino-2-chloro benzoic acid, MFCD00007845, SBB063085, NSC25172, zlchem 462, PubChem4654, AC1L1YMB, ACMC-209r1l, SCHEMBL81564, KSC449K5R, 2-chloro-5-amino benzoic acid, 248258_ALDRICH, 532495_ALDRICH, AC1Q51L7, 2-chloro-5-(amino)benzoic acid, Benzoicacid, 5-amino-2-chloro-, CTK3E9558, ZLC0326, ATTERCOP-CHM AT135165, GVCFFVPEOLCYNN-UHFFFAOYSA-N, MolPort-000-141-583, WT051, ZINC152575, 2-amino-4-carboxy-5-chlorobenzene, 4-amino-2-carboxy-1-chlorobenzene, ACT11896, EINECS 201-916-5, ANW-39319, BBL027662, NSC 25172, NSC-25172, STK345955, AKOS000109248, AN-2196, AS01771, CS20208, MCULE-7035710598, RP09543, RTR-028113, TRA0018784, VZ30023, 89-54-3 5-amino-2-chlorobenzoic acid, AJ-12760, AK-36786, BR-36786, KB-22434, OR025672, SC-07213, AB1001928, DB-000370, KB-196610, ST2418605, TL8005775, TR-028113, AM20060233, BB 0245792, FT-0084624, FT-0619976, ST50408186, A10722, Q-9446, I01-0299, W-100372, 3B3-016283, InChI=1/C7H6ClNO2/c8-6-2-1-4(9)3-5(6)7(10)11/h1-3H,9H2,(H,10,11

Removed Synonyms

null, C7H6ClNO2, CID37879, CB10057, A1913

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