N,O-Dimethylhydroxylamine → 4-Fluoro-N-methoxy-N-methylbenzamide

HRID 626081Notes

Reaction equation

HRID 626081 reaction equation
[CH3:1][NH:2][O:3][CH3:4].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[NH4+].[Cl-]>C1COCC1>[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([N:2]([O:3][CH3:4])[CH3:1])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 25517Ammonium ChlorideHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 140693474-Fluoro-N-methoxy-N-methylbenzamideYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,O-dimethylhydroxylamine (1.51 mmol; 147 mg) in dry THF (3 mL), under argon, was added at −78° C. nbutyllithium 2.5M (3.02 mmol; 1.21 mL). The mixture was stirred minutes at −78° C., before addition of 4-fluorobenzoyl chloride (1.26 mmol; 150 μL). The reaction was stirred overnight at room temperature, then treated with saturated NH4Cl and extracted with ethyl acetate. Combined organic layers were washed with water, dried over Na2SO4 and concentrated in vacuo, to give the title compound (66%; 173 mg) as a yellow oil used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washCombined organic layers were washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6db4e035a9544a5b8c64019800f1da42
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

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