Hydrazine hydrate (1:1) → HCID 23458543, compound

HRID 1679913Notes

Reaction equation

HRID 1679913 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C@H:8]2[CH2:10][C@H:9]2[C:11](O)=[O:12])=O)=[CH:4][CH:3]=1.O.[NH2:17][NH2:18]>C(O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]2[CH:8]3[CH:9]([C:11](=[O:12])[NH:17][N:18]=2)[CH2:10]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54112244HCID 54112244, compound

Product 1

HCID 23458543HCID 23458543, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.0 g (26.7 millimoles) of cis-2-(p-chlorobenzoyl)-cyclopropanecarboxylic acid, 1.47 g (29.4 millimoles) of hydrazine hydrate and 150 ml of ethanol are refluxed for 6 hours. The mixture is concentrated to about 20 ml and the product is filtered off at 0° C. and recrystallized from methanol. 4.7 g (80% of theory) of 2-(p-chlorophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are obtained as colorless crystals, of melting point 199°-200° C.

Workup

  1. concentrationThe mixture is concentrated to about 20 ml
  2. filtrationthe product is filtered off at 0° C.
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2b81325868cb4480b27318084965563a
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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