3-(Cyclopropylamino)-4-nitrobenzonitrile → 4-Amino-3-(cyclopropylamino)benzonitrile

HRID 1048966Notes

Reaction equation

HRID 1048966 reaction equation
[CH:1]1([NH:4][C:5]2[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=2[N+:13]([O-])=O)[C:8]#[N:9])[CH2:3][CH2:2]1>CCO.[Pd]>[NH2:13][C:12]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[NH:4][CH:1]1[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 666833633-(Cyclopropylamino)-4-nitrobenzonitrile

Product 1

HCID 666847494-Amino-3-(cyclopropylamino)benzonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 3-(cyclopropylamino)-4-nitrobenzonitrile (2.0 g, 0.009 mol) in EtOH (20 ml) was hydrogenated using Pd/C for 2 h at room temperature. The reaction was filtered through CELITE® and the filter bed was thoroughly washed with EtOH. The resulting solution was concentrated to provide 4-amino-3-(cyclopropylamino) benzonitrile as a brownish solid. 1H NMR (400 MHz, DMSO-d6), δ: 6.92 (bs, 1H), 6.88-6.86 (d, J=8 Hz, 1H), 6.55-6.53 (d, J=8.4 Hz, 1H), 5.50 (bs, 1H), 5.44 (s, 2H), 2.36-2.34 (m, 1H), 0.76-0.71 (m, 2H), 0.39-0.34 (m, 2H). MS (M+1): 174.

Workup

  1. customfor 2 h
  2. customat room temperature
  3. filtrationThe reaction was filtered through CELITE®
  4. washthe filter bed was thoroughly washed with EtOH
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-71138d18cfed43699431855059dfa731
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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