7-chloro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one → 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

HRID 867559Notes

Reaction equation

HRID 867559 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH2:16][OH:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].C(Cl)Cl>[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[CH:16]=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 212899527-chloro-4,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198515847-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

18.0 g (64.8 mmol) of 7-chloro-4,5-dihydro-3-hydroxymethyl-5methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 75 g of manganese dioxide and 700 ml of methylene chloride are stirred at room temperature for 1.5 hours. The reaction mixture is filtered and the filtrate is evaporated. By recrystallization of the residue from alcohol there is obtained 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxaldehyde of melting point 204°-205°.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. customBy recrystallization of the residue from alcohol

Sources & evidence

ORD record
ord-73709b47a02c461482d032f18ff8f961
Source dataset
uspto-grants-1988_10
Patent number
US04775671

Reaction notes

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