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

HRID 1679922Notes

Reaction equation

HRID 1679922 reaction equation
O.[N+:2]([C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[C:8]([C@H:10]1[CH2:12][C@H:11]1[C:13](O)=[O:14])=O)([O-:4])=[O:3].O.[NH2:20][NH2:21]>C(O)C>[N+:2]([C:5]1[CH:6]=[C:7]([C:8]2[CH:10]3[CH:11]([C:13](=[O:14])[NH:20][N:21]=2)[CH2:12]3)[CH:16]=[CH:17][CH:18]=1)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 70572351HCID 70572351, compound

Product 1

HCID 234585112-(m-Nitrophenyl)-3,4-diazabicyclo[4.1.0]hept-2-en-5-oneYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.4 g (17.4 millimoles) of cis-2-(m-nitrobenzoyl)-cyclopropanecarboxylic acid hydrate, 1.05 g (21.0 millimoles) of hydrazine hydrate and 100 ml of ethanol are refluxed for 7 hours. After filtering off the product at 10° C. and drying it under reduced pressure at 50° C., 2.8 g (70% of theory) of 2-(m-nitrophenyl)-3,4-diazabicyclo[4.1.0]hept-2-en-5-one are obtained as pale yellow crystals, of melting point 220°-221° C.

Workup

  1. filtrationAfter filtering off the product at 10° C.
  2. customdrying it under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-68531da51cac4caeb30ce8eb77465da5
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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