(2-Chloro-4-nitro-benzyl)-diethyl-amine → 3-Chloro-4-diethylaminomethyl-phenylamine

HRID 898545Notes

Reaction equation

HRID 898545 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:3]=1[CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7]>[Ni].C1COCC1>[Cl:1][C:2]1[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:3]=1[CH2:4][N:5]([CH2:8][CH3:9])[CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 68876192(2-Chloro-4-nitro-benzyl)-diethyl-amine

Product 1

HCID 287218213-Chloro-4-diethylaminomethyl-phenylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 0.700 g (2.884 mmol) (2-chloro-4-nitro-benzyl)-diethyl-amine (Z35a) and 0.400 g Raney nickel in 20 mL THF was hydrogenated for 7.5 h at RT and 25 psi. The catalyst was filtered off and the filtrate was evaporated down i. vac. The crude product was purified by column chromatography (Alox, neutral, act. II-III, petroleum ether/EtOAc 4:1).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down i
  3. customThe crude product was purified by column chromatography (Alox, neutral, act. II-III, petroleum ether/EtOAc 4:1)

Sources & evidence

ORD record
ord-46dbcf91156446f79b5ae9e1508b92ab
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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