Acetic Anhydride → N-[2-(3-fluoro-2-hydroxyphenyl)ethyl]acetamide

HRID 1712395Notes

Reaction equation

HRID 1712395 reaction equation
[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[F:1][C:2]1[C:3]([OH:11])=[C:4]([CH2:8][CH2:9][NH:10][C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 684994132-(3-Fluoro-2-hydroxyphenyl)acetonitrile

Product 1

HCID 68502069N-[2-(3-fluoro-2-hydroxyphenyl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.54 g of (3-fluoro-2-hydroxyphenyl)acetonitrile, 1.87 ml of acetic anhydride and 2.41 g of nickel chloride hexahydrate in 75 ml of methanol is admixed at 0° C. with 2.72 g of sodium borohydride in portions and stirred at room temperature over 22 hours. The reaction mixture is concentrated by evaporation, and the residue is diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution and clarified by filtration. The aqueous phase is extracted with ethyl acetate (3×). The combined organic phases are dried with sodium sulphate and concentrated by evaporation. The title compound is obtained as a beige solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.23 (95:5 dichloromethane-methanol); Rt=2.60.

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. additionthe residue is diluted with ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. filtrationclarified by filtration
  4. extractionThe aqueous phase is extracted with ethyl acetate (3×)
  5. dry with materialThe combined organic phases are dried with sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2c5d81497ccf4f35ac014243d08d01a8
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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