HCID 19357519, compound → 2-amino-N-methyl-N-phenylacetamide

HRID 377138Notes

Reaction equation

HRID 377138 reaction equation
[CH3:1][N:2]([C:9](=[O:14])[CH2:10][N+:11]([O-])=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H]>[Pd]>[CH3:1][N:2]([C:9](=[O:14])[CH2:10][NH2:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 19357519HCID 19357519, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 117688992-amino-N-methyl-N-phenylacetamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 5.0 g (0.026 moles) N-methyl 2-nitro acetanilide in 250 mL absolute alcohol is added 0.5 g of 10% palladium on activated carbon. The nitro functional group is reduced to amino functionality under catalytic reduction with hydrogen gas in a pressure bottle at 60 PSI using Parr hydrogenation apparatus. The reduction is carried out for five hours by which time the reaction is complete as indicated by no further consumption of H2 gas. The reaction mixture is filtered and the solvent from the filtrate is removed under reduced pressure. To the crude residue a small amount of mixture of ethyl acetate ethanol is added and cooled. The resulting precipitate is filtered and washed with cold ethyl acetate in ethanol solvent and dried to give the desired compound N-methyl 2-amino acetanilide.

Workup

  1. customas indicated by no further consumption of H2 gas
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent from the filtrate is removed under reduced pressure
  4. additionTo the crude residue a small amount of mixture of ethyl acetate ethanol
  5. additionis added
  6. temperaturecooled
  7. filtrationThe resulting precipitate is filtered
  8. washwashed with cold ethyl acetate in ethanol solvent
  9. customdried

Sources & evidence

ORD record
ord-63ae1009af364344b143539e19e660ea
Source dataset
uspto-grants-2000_02
Patent number
US06024937

Reaction notes

Loading…