2-Acetamido-6-chlorobenzoic acid → HCID 53444447, compound

HRID 1885965Notes

Reaction equation

HRID 1885965 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:11]C(C)=O)[CH:5]=[CH:4][CH:3]=1>Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([NH2:11])[C:7]=1[C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 880442-Acetamido-6-chlorobenzoic acid

Product 1

HCID 53444447HCID 53444447, compoundYield 209.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 20.0 grams (0.093 mole) of 6-chloro-2-(methylcarbonylamino)benzoic acid in 150 mL of concentrated hydrochloric acid was stirred at 80° for about 3 hours. The reaction mixture was cooled to ambient temperature and was filtered to collect a solid. The solid was washed with cold diethyl ether and dried to yield 20.3 grams of 6-chloroanthranilic acid hydrochloride; m.p. 194°-195° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. filtrationwas filtered
  2. customto collect a solid
  3. washThe solid was washed with cold diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-e801423cdd2448cebe8ec3c4e2b27195
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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