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

HRID 1606950Notes

Reaction equation

HRID 1606950 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]([CH3:18])[CH2:8][C:7]=12>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:18][N:9]1[C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:6]2[CH:5]=[N:4][C:3]([CH:2]=[O:1])=[C:7]2[CH2:8]1

Participants

4

Reactant 1

HCID 198516024,5-dihydro-3-(hydroxymethyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 198330205,6-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

6.73 g (27.6 mmol) of 4,5-dihydro-3-hydroxymethyl-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was stirred at room temperature for 4 hours together with 33 g (380 mmol) of manganese dioxide in 100 ml of methylene chloride. The mixture was filtered, the filter residue was rinsed thoroughly with about 1.5 l of methylene chloride and the filtrate was evaporated. There was obtained 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3--carboxaldehyde of melting point 202°-203°.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filter residue was rinsed thoroughly with about 1.5 l of methylene chloride
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-bbe40a1e79ff482cbfb385f290651eeb
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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