Methanol → 6-(2-Chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

HRID 26056Notes

Reaction equation

HRID 26056 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([Cl:27])=[N:21][C:22]([C:23]([O:25]C)=[O:24])=[C:11]2[CH2:10][N:9]=1.[OH-].[K+].CO>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=2[N:12]2[C:20]([Cl:27])=[N:21][C:22]([C:23]([OH:25])=[O:24])=[C:11]2[CH2:10][N:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 541351956-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid methyl ester

Product 1

HCID 203945756-(2-Chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2 g (0.005 mole) of 6-(2-chlorophenyl)-1,8-dichloro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid, methyl ester 0.7 g (0.012 mole) of potassium hydroxide, 60 ml of methanol and 2 ml of water was refluxed under argon for 2.5 hrs. The solution was evaporated in vacuo at 50°-60°. An aqueous solution of the residue was acidified with acetic acid to give a gelatinous, white precipitate. The precipitate was collected by filtration, washed with water and air dried on the funnel overnight to give off-white solid. Recrystallization from a solution of ethanol and methylene chloride gave white plates with mp 250°-253° (dec).

Workup

  1. customThe solution was evaporated in vacuo at 50°-60°
  2. customto give a gelatinous, white precipitate
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water and air
  5. customdried on the funnel overnight
  6. customto give off-white solid
  7. customRecrystallization from a solution of ethanol and methylene chloride
  8. customgave white plates with mp 250°-253° (dec)

Sources & evidence

ORD record
ord-0b2afd9e16bc41d9b8d881ddeeb1beb8
Source dataset
uspto-grants-1979_04
Patent number
US04147875

Reaction notes

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