N,N-Dimethyl-4-nitrobenzylamine → Benzenemethanamine, 4-amino-N,N-dimethyl-

HRID 1701471Notes

Reaction equation

HRID 1701471 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][CH:6]=1)[CH3:3]>[C].[Pd].C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 1

HCID 278498N,N-Dimethyl-4-nitrobenzylamine

Product 1

HCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×

Procedure

In a 30 l autoclave was placed a suspension in which 10 g. of a palladium-carbon catalyst was suspended in 50 ml of ethanol, and 890 g. of N,N-dimethyl-p-nitrobenzylamine and 10 l of ethanol were charged thereinto. Then, hydrogenation was carried out at 35° C. under 30 atm., and when the consumption of hydrogen was ceased, the reaction mixture was taken out of the autoclave. After the palladium-carbon was removed by filtration and the ethanol was removed by distillation to concentrate the filtrate, the resulting residue was distilled under reduced pressure to give a light-yellow liquid which was the desired product boiling at 105° to 108° C./2 mmHg. Yield: 675 g. (90%)

Workup

  1. customwas carried out at 35° C. under 30 atm., and when
  2. customthe consumption of hydrogen
  3. customAfter the palladium-carbon was removed by filtration
  4. customthe ethanol was removed by distillation
  5. concentrationto concentrate the filtrate
  6. distillationthe resulting residue was distilled under reduced pressure
  7. customto give a light-yellow liquid which

Sources & evidence

ORD record
ord-7b2a8f00b9f1488bbf5aef3da4148e3c
Source dataset
uspto-grants-1980_03
Patent number
US04193800

Reaction notes

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