Cyclohexene → (E)-N'-(4-Amino-2-cyanophenyl)-N,N-dimethylformimidamide

HRID 240537Notes

Reaction equation

HRID 240537 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[N:12]=[CH:13][N:14]([CH3:16])[CH3:15])#[N:2].C1CCCCC=1>CO.[Pd]>[NH2:9][C:7]1[CH:6]=[CH:5][C:4]([N:12]=[CH:13][N:14]([CH3:15])[CH3:16])=[C:3]([C:1]#[N:2])[CH:8]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 10900084N'-(2-cyano-4-nitrophenyl)-N,N-dimethylmethanimidamide

Product 1

HCID 11263933(E)-N'-(4-Amino-2-cyanophenyl)-N,N-dimethylformimidamideYield 90.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of N′-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine (30.0 g, 137 mmol), cyclohexene (200 mL) and 10% Pd on carbon (3.0 g) in methanol (1 L) was refluxed for 10 hours under a hydrogen atmosphere. The hot solution was filtered through Celite and the filtrate was concentrated under reduced pressure. The residue was recrystallized from dichloromethane/carbon tetrachloride to provide the product (23.4 g, 90%) as pale gray crystals.

Workup

  1. filtrationThe hot solution was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from dichloromethane/carbon tetrachloride

Sources & evidence

ORD record
ord-18bf35eb8dd443d18712fea0af66e94f
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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