Hydrazine hydrate (1:1) → HCID 23458522, compound

HRID 1679925Notes

Reaction equation

HRID 1679925 reaction equation
O.NN.[N+:4]([C:7]1[CH:8]=[C:9]([C:13]2[CH:14]3[CH:16]([C:17](=[O:20])[NH:18][N:19]=2)[CH2:15]3)[CH:10]=[CH:11][CH:12]=1)([O-])=O>C(O)C.[Ni]>[NH2:4][C:7]1[CH:8]=[C:9]([C:13]2[CH:14]3[CH:16]([C:17](=[O:20])[NH:18][N:19]=2)[CH2:15]3)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 234585112-(m-Nitrophenyl)-3,4-diazabicyclo[4.1.0]hept-2-en-5-one

Product 1

HCID 23458522HCID 23458522, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 0.65 g (13.0 millimoles) of hydrazine hydrate in 10 ml of ethanol is added, whilst stirring, to a mixture of 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), 20 ml of ethanol and a small amount of an aqueous Raney nickel suspension in the course of 5 minutes, during which the temperature rises from 25° to 35° C. Stirring is continued for 1 hour and the reaction mixture is then slowly raised to the boil. It is refluxed for 5 minutes and filtered hot, and the filtrate is concentrated. After recrystallization from ethyl acetate/methanol, 1.0 g (76% of theory) of 2-(m-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one is obtained as colorless crystals, identical with the compound from Example 33.

Workup

  1. customin the course of 5 minutes
  2. customrises from 25° to 35° C
  3. temperaturethe reaction mixture is then slowly raised to the boil
  4. temperatureIt is refluxed for 5 minutes
  5. filtrationfiltered hot
  6. concentrationthe filtrate is concentrated
  7. customAfter recrystallization from ethyl acetate/methanol

Sources & evidence

ORD record
ord-76815d093611414aaacc6057aa4facfb
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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