4-(Cyclohexylamino)-3-nitrobenzonitrile → 3-Amino-4-(cyclohexylamino)benzonitrile

HRID 392958Notes

Reaction equation

HRID 392958 reaction equation
[CH:1]1([NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[N+:16]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.CO.[Pd]>[NH2:16][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:8]=1[NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[C:12]#[N:13]

Participants

5

Reactant 1

HCID 29852004-(Cyclohexylamino)-3-nitrobenzonitrile

Product 1

HCID 226608193-Amino-4-(cyclohexylamino)benzonitrileYield 99.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 3 (1.23 g, 5.01 mmol) in ethyl acetate (30 mL) and methanol (10 mL) was hydrogenated over 10% palladium on carbon (0.11 g) at 20 psi for 1 h. The reaction mixture was filtered and concentrated on a rotary evaporator to give compound 4 (1.07 g, 99%) as a red-brown solid. ESI-MS m/e 216.3 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-ebf93c5e67234924a2fd8ea7399ab5aa
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

Loading…