Hydrazine hydrate (1:1) → 2-(p-Acetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one

HRID 1679914Notes

Reaction equation

HRID 1679914 reaction equation
[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]([C@H:11]2[CH2:13][C@H:12]2[C:14](O)=[O:15])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].O.[NH2:20][NH2:21]>C(O)C>[C:1]([NH:4][C:5]1[CH:18]=[CH:17][C:8]([C:9]2[CH:11]3[CH:12]([C:14](=[O:15])[NH:20][N:21]=2)[CH2:13]3)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54059416cis-2-(p-Acetylaminobenzoyl)-cyclopropanecarboxylic acid

Product 1

HCID 234585282-(p-Acetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-oneYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.0 g (24.3 millimoles) of cis-2-(p-acetylaminobenzoyl)-cyclopropanecarboxylic acid, 1.33 g (26.6 millimoles) of hydrazine hydrate and 150 ml of ethanol are refluxed for 6 hours. After filtering off the product at 0° C. and drying it under reduced pressure at 50° C., 5.0 g (85% of theory) of 2-(p-acetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are isolated as colorless crystals, melting point 269°-270° C. after recrystallization from a methanol/water mixture.

Workup

  1. filtrationAfter filtering off the product at 0° C.
  2. customdrying it under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-378265ba10f24c519e063e8f71ec98d1
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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