Acetic Anhydride → N-(3-fluoro-2-methylphenyl)acetamide

HRID 1830007Notes

Reaction equation

HRID 1830007 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH3:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(Cl)Cl>[F:8][C:4]1[C:3]([CH3:9])=[C:2]([NH:1][C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2855533-Fluoro-2-methylaniline

Product 1

HCID 1489284N-(3-fluoro-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-amino-3-fluoro-2-methylbenzene (1 equivalent) was dissolved in CH2Cl2 and acetic anhydride (2.0 equivalents) was added slowly. The solution was stirred at room temperature for 4 hours. The reaction mixture was then quenched with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with H2O, a 10% HCl solution, H2O, and brine. It was then dried over Na2SO4 and concentrated in vacuo, to yield N-(3-fluoro-2-methylphenyl)acetamide as a pink solid. LC/MS (m/z) 168.2 (MH+), Rt 1.91 minutes.

Workup

  1. customThe reaction mixture was then quenched with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was washed with H2O
  4. dry with materialIt was then dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8238e89799944c5694d8826358b1f0d3
Source dataset
uspto-grants-2006_06
Patent number
US07064215B2

Reaction notes

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