Ethanol → 7-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

HRID 223197Notes

Reaction equation

HRID 223197 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18]CC)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[Na+]>O>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([OH:18])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 71231Sarmazenil

Product 1

HCID 145904217-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3.11 g (9.72 mmol) of ethyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 10 ml of ethanol, 2 ml of water and 400 mg of sodium hydroxide is heated to boiling under reflux for 1 hour. After evaporation of the ethanol, the residue is treated with 10 ml of 1 N hydrochloric acid. The colourless material obtained is filtered off under suction, washed with water and dried. There is obtained 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid with a decomposition point of 283°-284°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1 hour
  3. customAfter evaporation of the ethanol
  4. additionthe residue is treated with 10 ml of 1 N hydrochloric acid
  5. customThe colourless material obtained
  6. filtrationis filtered off under suction
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-04d660b749e44f96b13eb7d1e2871a9f
Source dataset
uspto-grants-1982_10
Patent number
US04352818

Reaction notes

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