Methanol → 4-Chloro-2-cyclopropylamino-5-fluoro-benzoic acid

HRID 2270233Notes

Reaction equation

HRID 2270233 reaction equation
C([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([Cl:12])=[CH:7][C:6]=1[NH:13][CH:14]1[CH2:16][CH2:15]1)C.[Li+].[OH-].CO>C1COCC1>[Cl:12][C:8]1[C:9]([F:11])=[CH:10][C:5]([C:4]([OH:17])=[O:3])=[C:6]([NH:13][CH:14]2[CH2:15][CH2:16]2)[CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 543590154-Chloro-2-cyclopropylamino-5-fluoro-benzoic acid ethyl ester

Product 1

HCID 226328834-Chloro-2-cyclopropylamino-5-fluoro-benzoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-2-cyclopropylamino-5-fluoro-benzoic acid ethyl ester (Example B-3, 4.10 g, 15.9 mmol) in THF (100 mL) was reacted with an aqueous solution of 1.0 N LiOH (45 mL, 45 mmol) and methanol (40 mL) and allowed to stir overnight. The mixture was then concentrated to one-third volume and acidified with 1.0 N HCl. The mixture was extracted with ethyl acetate. the organic layers combined, dried with sodium sulfate, and concentrated to provide 3.0 g of the title compound as an oil.

Workup

  1. concentrationThe mixture was then concentrated to one-third volume
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d9d12f465747472eaa14154960d0876d
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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