Acetic Anhydride → N-(3-fluoro-2-formyl-phenyl)-acetamide

HRID 1294566Notes

Reaction equation

HRID 1294566 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH:4]=[O:5].[C:11](OC(=O)C)(=[O:13])[CH3:12].C([O-])([O-])=O.[Na+].[Na+]>O>[F:10][C:6]1[C:3]([CH:4]=[O:5])=[C:2]([NH:1][C:11](=[O:13])[CH3:12])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 217194752-Amino-6-fluorobenzaldehyde

Product 1

HCID 23106215N-(3-fluoro-2-formyl-phenyl)-acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1.37 g (9.85 mmol) 2-amino-6-fluoro-benzaldehyde are combined with 20 ml acetic anhydride and heated to 70° C. for 4 h. Then the reaction mixture is stirred into 200 ml dist. water, adjusted to pH 7 with Na2CO3 and extracted three times with 50 ml of ethyl acetate. Then the organic phase is dried with MgSO4, the solvent is eliminated in vacuo. The crude product is purified by column chromatography. The carrier material used is silica gel and the eluant used is a mixture of cyclohexane:ethyl acetate (80:20).

Workup

  1. extractionextracted three times with 50 ml of ethyl acetate
  2. dry with materialThen the organic phase is dried with MgSO4
  3. customThe crude product is purified by column chromatography
  4. additiona mixture of cyclohexane:ethyl acetate (80:20)

Sources & evidence

ORD record
ord-e14bf518de48403ea3cdb852d790be81
Source dataset
uspto-grants-2007_07
Patent number
US07241769B2

Reaction notes

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