4-Bromo-2-methylaniline → N-(4-bromo-2-methylphenyl)-3-oxobutanamide

HRID 986012Notes

Reaction equation

HRID 986012 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[CH2:10]=[C:11]1[O:15][C:13](=[O:14])[CH2:12]1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:13](=[O:14])[CH2:12][C:11]([CH3:10])=[O:15])=[C:4]([CH3:9])[CH:3]=1

Participants

4

Reactant 2

HCID 114234-Bromo-2-methylanilineHCID 12661Diketene

Product 1

HCID 4100579N-(4-bromo-2-methylphenyl)-3-oxobutanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromo-2-methylaniline (25 g) and diketene (11.8 cm3) in toluene (100 cm3) was heated with stirring under reflux for 5 hours. On cooling to room temperature the precipitated solid was filtered off and recrystallised from hexane/ethyl acetate to afford N-[4-bromo-2-methylphenyl]-acetoacetamide, m.p. 109° (14.0 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationwas filtered off
  4. customrecrystallised from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4d8422dc2bed486d8ed9e4a7451c3bc9
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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