2-(m-Nitrophenyl)-3,4-diazabicyclo[4.1.0]hept-2-en-5-one → HCID 23458522, compound

HRID 1679924Notes

Reaction equation

HRID 1679924 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]=1

Participants

4

Reactant 1

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

Product 1

HCID 23458522HCID 23458522, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customWhen the hydrogen absorption
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated
  4. customThe residue is recrystallized from an ethyl acetate/methanol mixture

Sources & evidence

ORD record
ord-5af43b8c4c4e406e9d64055ff8542ed9
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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