Hydrochloric Acid → 6-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid

HRID 1723683Notes

Reaction equation

HRID 1723683 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:9]([C:10](=[O:12])[CH3:11])=[CH:8][C:7]([F:13])=[C:6]([F:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22].[Li+].[OH-].Cl>C1COCC1.O>[C:10]([C:9]1[C:4]([C:3]([OH:23])=[O:2])=[C:5]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:6]([F:14])=[C:7]([F:13])[CH:8]=1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 865985946-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

Product 1

HCID 860527646-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acidYield 86.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 6-acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (200 mg, 0.59 mmol) in THF-water (2 mL/0.5 mL) was added 1 M aqueous LiOH (1.21 mL, 1.21 mmol) at room temperature. The reaction mixture was stirred for 30 minutes, acidified to pH 1 with 1 N aqueous HCl, and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to give the desired acid (166 mg, 86%) that was used directly without further purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01c3dbec73a744038e92c3705fa54dc8
Source dataset
uspto-grants-2009_02
Patent number
US07485643B2

Reaction notes

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