Sodium Hydroxide → HCID 68699281, compound

HRID 2244370Notes

Reaction equation

HRID 2244370 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([F:12])[C:6]=1[N:13](C(=O)C)[C:14](=[O:16])[CH3:15])C.[OH-].[Na+]>CO.C(OCC)(=O)C.O>[C:14]([NH:13][C:6]1[C:7]([F:12])=[CH:8][C:9]([Cl:11])=[CH:10][C:5]=1[C:4]([OH:20])=[O:3])(=[O:16])[CH3:15]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 68699564HCID 68699564, compound

Product 1

HCID 68699281HCID 68699281, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-2-diacetylamino-3-fluorobenzoic acid ethyl ester (185 mg, 0.61 mmol) in MeOH (4 ml) was added 1N NaOH (1288 μl, 1.29 mmol) and the reaction mixture was refluxed for 2 h. The reaction mixture was cooled to RT and then diluted with ethyl acetate and water. The organic phase was separated and the aqueous phase was made acidic with 1N HCl to pH3 and then extracted with ethyl acetate (2×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the desired product (130 mg, 92%) as a white solid which did not require further purification. MS (ISP) 230.1 (M−H)−.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customThe organic phase was separated
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-948086a1ee274e4a9aa22a61ec2e1242
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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