Methyl Anthranilate → HCID 17564401, compound

HRID 643994Notes

Reaction equation

HRID 643994 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:14]([O:23][CH3:24])(=[O:22])[C:15]1[C:16](=[CH:18][CH:19]=[CH:20][CH:21]=1)[NH2:17]>C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>[C:9]([C:8]1[CH:12]=[CH:13][C:5]([S:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[C:14]([O:23][CH3:24])=[O:22])(=[O:4])=[O:3])=[CH:6][CH:7]=1)([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 8635Methyl AnthranilateHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 17564401HCID 17564401, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 11430Potassium CarbonateSolvent

Procedure

4-Chlorosulfonylbenzoic acid (2.21 g, 10 mmol) is added to a solution of the methyl anthranilate (1.51 g, 10 mmol) in 20 mL of DCM at RT. The reaction is stirred 16 h and then filtered to give a white solid. The solid is dissolved in diluted aqueous potassium carbonate and extracted with EtOAc. The aqueous phase is added slowly to an excess (25 mL) of 1 N aqueous HCl. A white solid precipitates and is collected by filtration, washed with water, and dried under vacuum to give methyl 2-(4-carboxybenzene-sulfonylamino)-benzoate.

Workup

  1. filtrationfiltered
  2. customto give a white solid
  3. extractionextracted with EtOAc
  4. additionThe aqueous phase is added slowly to an excess (25 mL) of 1 N aqueous HCl
  5. customA white solid precipitates
  6. filtrationis collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-fb523b64d2fb4a4bb499c4f078421467
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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