Hydrochloric Acid → Methyl 4-chloroanthranilate

HRID 1090831Notes

Reaction equation

HRID 1090831 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.[CH3:13]O>>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH3:13])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 666462-Amino-4-chlorobenzoic acid

Product 1

HCID 80001Methyl 4-chloroanthranilate

Procedure

A solution of 10.0 g (58 mmol) of 4-chloroanthranilic acid in 100 ml of methanol was heated under reflux, while gaseous hydrogen chloride was blown through the heated solution for 2.5 hrs. After the heating was terminated, methanol was distilled off. The residue was shaken with chloroform and aqueous sodium carbonate. The organic phase was taken out and dried over anhydrous sodium sulfate. Chloroform was distilled off under reduced pressure to leave 9.68 g of the desired compound as a residual pale brown crystalline product.

Workup

  1. customAfter the heating was terminated
  2. distillationmethanol was distilled off
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationChloroform was distilled off under reduced pressure

Sources & evidence

ORD record
ord-ab53288701694f94b5a78ea349223b0e
Source dataset
uspto-grants-1992_01
Patent number
US05082943

Reaction notes

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