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

HRID 583100Notes

Reaction equation

HRID 583100 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-dimethylformimidamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6.0 g (27.5 mmol) of N'-(2-cyano-4-nitrophenyl)-N,N-dimethylformamidine, 33.9 g (41.8 ml, 412.4 mmol) of cyclohexene, and 0.6 g of 10% Pd/C in 360 ml of methanol was refluxed for 4 hrs. The hot mixture was filtered through Celite. Solvent was removed and the residue was recrystallized from chloroform-carbon tetrachloride giving 4.9 g (95%) of the tide compound as a light gray crystalline solid. mass spectrum (m/e): 188.9 (M+H, electrospray).

Workup

  1. filtrationThe hot mixture was filtered through Celite
  2. customSolvent was removed
  3. customthe residue was recrystallized from chloroform-carbon tetrachloride giving 4.9 g (95%) of the tide compound as a light gray crystalline solid

Sources & evidence

ORD record
ord-5fdc38a0d30143cabef36c3e93a4c2a7
Source dataset
uspto-grants-1999_07
Patent number
US05929080

Reaction notes

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