Pyridine → Butanamide, N-(3-chlorophenyl)-3-oxo-

HRID 1165573Notes

Reaction equation

HRID 1165573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[CH2:15]=[C:16]1[O:20][C:18](=[O:19])[CH2:17]1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][C:18](=[O:19])[CH2:17][C:16]([CH3:15])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79323-ChloroanilineHCID 12661Diketene

Product 1

HCID 75487Butanamide, N-(3-chlorophenyl)-3-oxo-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolved in toluene were 2.5 g (0.02 mole) of m-chloroaniline and a catalytic amount of pyridine, followed by dropwise addition of 1.9 g (0.022 mole) of diketene at 50° C. After completion of the dropwise addition, the resultant mixture was heated under reflux for 3 hours. Under ice-cooling, ligroin was added, and precipitated crystals were collected by filtration and were then washed first with ligroin and then with hexane. The crystals were then dried under reduced pressure to obtain 3'-chloroacetoacetanilide.

Workup

  1. additionAfter completion of the dropwise addition
  2. temperatureunder reflux for 3 hours
  3. temperatureUnder ice-cooling
  4. customprecipitated crystals
  5. filtrationwere collected by filtration
  6. washwere then washed first with ligroin
  7. customThe crystals were then dried under reduced pressure

Sources & evidence

ORD record
ord-93cdf8a934024410bf797b669fefe2f4
Source dataset
uspto-grants-1990_03
Patent number
US04910315

Reaction notes

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