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

HRID 867522Notes

Reaction equation

HRID 867522 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.[OH-].[Na+].C(O)C.Cl>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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 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 37.3 g (116.6 mmol) of ethyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 5.276 g (131.9 mmol) of sodium hydroxide, 150 ml of ethanol and 100 ml of water is heated to boiling under reflux for 15 minutes. The mixture is then neutralized by the addition of 132 ml of 1N hydrochloric acid, the ethanol is distilled off in vacuo and the residue is diluted with 100 ml of water. The mixture is cooled to about 0°, the product is filtered off under suction, rinsed with water and dried at 80° in a high vacuum. There is obtained 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid of decomposition point 283°-284°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 minutes
  3. distillationthe ethanol is distilled off in vacuo
  4. additionthe residue is diluted with 100 ml of water
  5. temperatureThe mixture is cooled to about 0°
  6. filtrationthe product is filtered off under suction
  7. washrinsed with water
  8. customdried at 80° in a high vacuum

Sources & evidence

ORD record
ord-705a3bfe427244c19dd243dfb7dfca2a
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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