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

HRID 1894669Notes

Reaction equation

HRID 1894669 reaction equation
[F:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>C(Cl)Cl>[F:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 2855533-Fluoro-2-methylaniline

Product 1

HCID 1489284N-(3-fluoro-2-methylphenyl)acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-2-methylaniline (6.00 g, 48 mmol) in dry DCM (100 mL) under nitrogen was added acetic anhydride (7.6 g, 75 mmol). The reaction mixture was stirred at r.t. for 18 h then washed with water (2×50 mL) and NaOH solution (1M, 2×50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the title compound (8.0 g, 100%) as a white solid. δH (CDCl3) 7.56 (1H, s), 7.16 (1H, q, J=7.6 Hz), 6.99 (1H, br s), 6.87 (1H, t, J=8.4 Hz), 2.27 (3H, s), 2.16 (3H, s).

Workup

  1. washthen washed with water (2×50 mL) and NaOH solution (1M, 2×50 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ac1f903b2e74d1c9e434a531a67ba84
Source dataset
uspto-grants-2013_08
Patent number
US08513284B2

Reaction notes

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