4,5-dihydro-3-(1-hydroxypropyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one → 4,5-dihydro-5-methyl-3-propionyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

HRID 67610Notes

Reaction equation

HRID 67610 reaction equation
[OH:1][CH:2]([C:5]1[N:6]=[CH:7][N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12](=[O:19])[N:11]([CH3:20])[CH2:10][C:9]=12)[CH2:3][CH3:4]>[O-2].[O-2].[Mn+4].C(Cl)Cl>[CH3:20][N:11]1[C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:8]2[CH:7]=[N:6][C:5]([C:2](=[O:1])[CH2:3][CH3:4])=[C:9]2[CH2:10]1

Participants

4

Reactant 1

HCID 205153284,5-dihydro-3-(1-hydroxypropyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one

Product 1

HCID 205153154,5-dihydro-5-methyl-3-propionyl-6H-imidazo[1,5-a][1,4]-benzodiazepin-6-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.84 g (6.8 mmol) of 4,5-dihydro-3-(1-hydroxypropyl)-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one, 16 g of manganese dioxide and 150 ml of methylene chloride is stirred at room temperature under an argon atmosphere for 2 hours. The manganese dioxide is filtered off under suction over a glass filter and the filtrate is evaporated in vacuo. After recrystallisation of the residue from 100 ml of ethyl acetate, there is obtained 4,5-dihydro-5-methyl-3-propionyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 215°-216° C.

Workup

  1. filtrationThe manganese dioxide is filtered off under suction over a glass
  2. filtrationfilter
  3. customthe filtrate is evaporated in vacuo
  4. customAfter recrystallisation of the residue from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-7c3f9caa08054ef0b56ad903268f51b9
Source dataset
uspto-grants-1982_08
Patent number
US04346036

Reaction notes

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