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

HRID 450068Notes

Reaction equation

HRID 450068 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1>C(O)(=O)C.[Fe]>[CH3:13][N:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:10])=[CH:8][CH:9]=1)[CH3:1]

Participants

4

Reactant 1

HCID 278498N,N-Dimethyl-4-nitrobenzylamine

Product 1

HCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-Yield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of dimethyl-(4-nitro-benzyl)-amine (1 g, 5.55 mmol) in acetic acid (10 ml) was added activated iron powder (3 g) and the reaction mixture was stirred for 5 hr at 80° C. The reaction mixture was filtered; the filtrate diluted with water and neutralized with 10% sodium hydroxide solution. The product was extracted with ethyl acetate, the organic layer was dried and evaporated to give a residue. Purification by column chromatography using chloroform/methanol (98:2) to give 4-dimethylaminomethyl-phenylamine (0.7 g, 85%)

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate diluted with water and neutralized with 10% sodium hydroxide solution
  3. extractionThe product was extracted with ethyl acetate
  4. customthe organic layer was dried
  5. customevaporated
  6. customto give a residue
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-1429c5b3eecb4602840497df3c1bc329
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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