Sodium Hydroxide → HCID 68702449, compound

HRID 2244369Notes

Reaction equation

HRID 2244369 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([F:12])[C:6]=1[NH:13][CH3:14])C.[OH-].[Na+]>CO.C(OCC)(=O)C.O>[Cl:11][C:9]1[CH:8]=[C:7]([F:12])[C:6]([NH:13][CH3:14])=[C:5]([CH:10]=1)[C:4]([OH:15])=[O:3]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68697643HCID 68697643, compound

Product 1

HCID 68702449HCID 68702449, compoundYield 93.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-3-fluoro-2-methylaminobenzoic acid ethyl ester (135 mg, 0.58 mmol) in MeOH was added 1N NaOH (1165 μl, 1.17 mmol) and the reaction mixture was refluxed for 2 h. The reaction mixture was diluted with ethyl acetate and water and then extracted. The aqueous layer was acidified to pH3 using 1N HCl and the aqueous layer was extracted with EtOAc (2×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the desired product (110 mg, 93%) which did not require further purification. MS (ISP) 202.1 (M−H)−.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. extractionextracted
  3. extractionthe aqueous layer was extracted with EtOAc (2×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e4ef00ff7b5b47bd93c55340e493e384
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

Loading…