Formic Acid → 2-(p-Formylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one

HRID 1679917Notes

Reaction equation

HRID 1679917 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)=[CH:4][CH:3]=1.[CH:16](O)=[O:17]>O>[CH:16]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]3[CH:11]([C:12](=[O:15])[NH:13][N:14]=2)[CH2:10]3)=[CH:6][CH:7]=1)=[O:17]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

Product 1

HCID 234584852-(p-Formylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-oneYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.0 g (29.8 millimoles) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 8a) and 30 ml of formic acid are refluxed for 1 hour. The solution is then poured into 500 ml of water and the precipitate which separates out is filtered off, washed with water and recrystallized from a methanol/water mixture. 4.6 g (67% of theory) of 2-(p-formylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are isolated as almost colorless crystals, of melting point 239°-240° C.

Workup

  1. filtrationthe precipitate which separates out is filtered off
  2. washwashed with water
  3. customrecrystallized from a methanol/water mixture

Sources & evidence

ORD record
ord-f4e80b3f886f48a4bd15341391abca9c
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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