(2-Oxopropyl)amine → N-Acetylmethyl-nicotinamide

HRID 1650699Notes

Reaction equation

HRID 1650699 reaction equation
[NH2:1][CH2:2][C:3](=[O:5])[CH3:4].[C:6](Cl)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1>ClCCl>[C:3]([CH2:2][NH:1][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 215(2-Oxopropyl)amineHCID 82604Nicotinoyl chloride

Product 1

HCID 19612493N-Acetylmethyl-nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 40 g (0.370 mol) of aminoacetone in 500 ml of dry dichloromethane, 50 g (0.350 mol) of nicotinoyl chloride was added dropwise at room temperature under a nitrogen atmosphere. The mixture was refluxed 5 h followed by stirring overnight at room temperature. The colorless precipitate was collected by filtration and dissolved in 400 ml of water. After basification with ammonia the aqueous solution was extracted with 3×400 ml of dichloromethane. The combined organic phases were treated with charcoal and dried over magnesium sulphate. Removal of the solvent in vacuo gave a colorless solid, 73. Yield: 30.0 g (0.170 mol, 48%).

Workup

  1. additionwas added dropwise at room temperature under a nitrogen atmosphere
  2. temperatureThe mixture was refluxed 5 h
  3. filtrationThe colorless precipitate was collected by filtration
  4. dissolutiondissolved in 400 ml of water
  5. extractionAfter basification with ammonia the aqueous solution was extracted with 3×400 ml of dichloromethane
  6. additionThe combined organic phases were treated with charcoal
  7. dry with materialdried over magnesium sulphate
  8. customRemoval of the solvent in vacuo
  9. customgave a colorless solid, 73

Sources & evidence

ORD record
ord-fdf6ddecdb0c4ecdaea68f8d9b5f31be
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

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