2-(m-Nitrophenyl)-3,4-diazabicyclo[4.1.0]hept-2-en-5-one → HCID 23458522, compound
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>O1CCCC1.[Pd]>[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]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1.5 g (6.5 millimoles) of 2-(m-nitrophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 32b), dissolved in 80 ml of tetrahydrofuran, are hydrogenated with 0.5 g of 10% strength palladium on charcoal at room temperature. When the hydrogen absorption has ceased, the catalyst is filtered off and the filtrate is concentrated. The residue is recrystallized from an ethyl acetate/methanol mixture. 0.9 g (69% of theory) of 2-(m-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one is obtained as colorless crystals, which are identical with the compound from Example 33.