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

HRID 1679916Notes

Reaction equation

HRID 1679916 reaction equation
[NH2:1][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>[NH2:1][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 54423379HCID 54423379, compound

Product 1

HCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g (97.5 millimoles) of cis-2-(p-aminobenzoyl)-cyclopropanecarboxylic acid, 5.9 g (118 millimoles) of hydrazine hydrate and 100 ml of ethanol are refluxed for 5 hours. After filtering off the product at 10° C. and drying it under reduced pressure at 50° C., 18.6 g (95% of theory) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]-hept-2-en-5-one are obtained as pale yellow crystals, which are identical with the compound from Example 8a.

Workup

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

Sources & evidence

ORD record
ord-dbef9dabf2d14617a39615891871e46f
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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