N-(2-nitrophenyl)-2-dimethylaminoacetamide → N-(2-aminophenyl)-2-(dimethylamino)acetamide

HRID 1415635Notes

Reaction equation

HRID 1415635 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:16])[CH2:12][N:13]([CH3:15])[CH3:14])([O-])=O.[H][H]>[Pt]=O.C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:16])[CH2:12][N:13]([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 2958870N-(2-nitrophenyl)-2-dimethylaminoacetamideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 16784338N-(2-aminophenyl)-2-(dimethylamino)acetamideYield 77.8%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

N-(2-nitrophenyl)-2-dimethylaminoacetamide (13.8 g), platinum oxide (0.2 g) and ethanol (100 ml) were mixed together and shaken in an atmosphere of hydrogen at atmospheric pressure and laboratory temperature until absorption of hydrogen ceased (4.5 litres of hydrogen were absorbed in 2hours). The mixture was then filtered and the ethanol evaporated off under reduced pressure. The solid residue so obtained was recrystallised from cyclohexane to give N-(2-aminophenyl)-2-dimethylaminoacetamide (9.3 g), m.p. 121°-123° C.

Workup

  1. custom(4.5 litres of hydrogen were absorbed in 2hours)
  2. filtrationThe mixture was then filtered
  3. customthe ethanol evaporated off under reduced pressure
  4. customThe solid residue so obtained
  5. customwas recrystallised from cyclohexane

Sources & evidence

ORD record
ord-3c74c1875df44f629e9d42366603f025
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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