2-cyano-N,N-dihexyl-4-nitroaniline → 2-cyano-N1,N1-dihexylbenzene-1,4-diamine

HRID 56206Notes

Reaction equation

HRID 56206 reaction equation
[C:1]([C:3]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18][C:4]=1[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])#[N:2]>CO.[Pd]>[C:1]([C:3]1[CH:21]=[C:20]([NH2:22])[CH:19]=[CH:18][C:4]=1[N:5]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])#[N:2]

Participants

4

Reactant 1

HCID 900227722-cyano-N,N-dihexyl-4-nitroaniline

Product 1

HCID 1179660632-cyano-N1,N1-dihexylbenzene-1,4-diamineYield 59%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-cyano-N,N-dihexyl-4-nitroaniline (2.89 g, 8.72 mmol) and Pd/C (0.30 g) in MeOH (30 mL) under H2 was stirred at rt overnight. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as colorless oil (1.55 g, 59%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1)

Sources & evidence

ORD record
ord-fceacc3afdf14efb9c6ee7ecf21538bc
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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