Cyclohexylamine → 4-(Cyclohexylamino)-3-nitrobenzonitrile

HRID 392957Notes

Reaction equation

HRID 392957 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>C(#N)C>[CH:13]1([NH:19][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[N+:10]([O-:12])=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 13655Benzonitrile, 4-chloro-3-nitro-

Product 1

HCID 29852004-(Cyclohexylamino)-3-nitrobenzonitrileYield 90.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-chloro-3-nitrobenzonitrile (5.28 g, 28.9 mmol), cyclohexylamine (5.0 mL, 43.7 mmol), and triethylamine (6.0 mL, 43.0 mL) in acetonitrile (75 mL) was stirred at 50° C. for 15 h. The reaction mixture was cooled to rt and then poured into 100 mL ice water. The solid precipitate was filtered, washed with water, and dried to afford compound 3 as a yellow solid (6.42 g, 90%). ESI-MS m/e 246.3 (M+1).

Workup

  1. filtrationThe solid precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c55269046da2467e8d071ce3c0351aa2
Source dataset
uspto-grants-2004_10
Patent number
US06803374B2

Reaction notes

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