Cyclohexene → HCID 23458522, compound

HRID 1679923Notes

Reaction equation

HRID 1679923 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]3[CH:13]([C:14](=[O:17])[NH:15][N:16]=2)[CH2:12]3)[CH:7]=[CH:8][CH:9]=1)([O-])=O.C1CCCCC=1>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]3[CH:13]([C:14](=[O:17])[NH:15][N:16]=2)[CH2:12]3)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 234585112-(m-Nitrophenyl)-3,4-diazabicyclo[4.1.0]hept-2-en-5-one

Product 1

HCID 23458522HCID 23458522, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

20.4 g (88.2 millimoles) of 2-(m-nitrophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 32b), 300 ml of ethanol, 150 ml of cyclohexene and 4.2 g of 10% strength palladium on charcoal are refluxed for 12 hours. The catalyst is filtered off, the filtrate is concentrated and the residue is recrystallized from ethyl acetate/methanol. 8.5 g (48% of theory) of 2-(m-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are obtained as beige crystals, of melting point 192°-193° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated
  3. customthe residue is recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-9a02c63c1713461489267f8461c4592f
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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