Hydrochloric Acid → 5-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-one

HRID 1679915Notes

Reaction equation

HRID 1679915 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]3[CH:14]([C:15](=[O:18])[NH:16][N:17]=2)[CH2:13]3)=[CH:7][CH:6]=1)(=O)C.CO.[OH-].[Na+].Cl>O>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]3[CH:14]([C:15](=[O:18])[NH:16][N:17]=2)[CH2:13]3)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 14798Sodium HydroxideHCID 234585282-(p-Acetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one

Product 1

HCID 202648445-(4-Aminophenyl)-3,4-diazabicyclo[4.1.0]hept-4-en-2-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25 g (103 millimoles) of 2-(p-acetylaminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one (see Example 7c), 215 ml of methanol and 215 ml of 10 N sodium hydroxide solution are refluxed for 3 hours. The methanol is then stripped off under reduced pressure. 500 ml of water are added to the residue and the mixture is brought to pH 4 with dilute hydrochloric acid. After filtering off the product and drying it under reduced pressure at 50° C., 19.3 g (93% of theory) of 2-(p-aminophenyl)-3,4-diaza-bicyclo[4.1.0]hept-2-en-5-one are isolated as almost colorless crystals, of melting point 230°-231° C. after recrystallization from methanol.

Workup

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

Sources & evidence

ORD record
ord-3b63111a158d4d3397af6608cbe2bf4c
Source dataset
uspto-grants-1981_06
Patent number
US04271163

Reaction notes

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