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

HRID 1606949Notes

Reaction equation

HRID 1606949 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[N:15][C:16]([C:17](OCC)=[O:18])=[C:4]2[CH2:3]1.[BH4-].[Li+].Cl.N>O1CCCC1.O>[OH:18][CH2:17][C:16]1[N:15]=[CH:14][N:5]2[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8](=[O:9])[N:2]([CH3:1])[CH2:3][C:4]=12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 127597Ro 14-7437HCID 4148881Lithium borohydride

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

14.14 g (49.5 mmol) of ethyl 5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate in 100 ml of tetrahydrofuran were treated portionwise at the boiling temperature with 1.35 g (62 mmol) of lithium borohydride, whereupon the mixture was boiled at reflux for 6 hours. The reaction mixture was then cooled, a mixture of 20 ml of water and 20 ml of concentrated hydrochloric acid was cautiously added thereto, the mixture was heated, stirred at the boiling temperature for 30 minutes, again cooled and treated with concentrated ammonia until the reaction was alkaline. The organic solvent was distilled off on a rotary evaporator and the aqueous suspension obtained was cooled and filtered. The filter residue was washed with water and dried. There was obtained 4,5-dihydro-3-hydroxymethyl-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 219°-221°.

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureThe reaction mixture was then cooled
  3. additionwas cautiously added
  4. temperaturethe mixture was heated
  5. temperatureagain cooled
  6. distillationThe organic solvent was distilled off on a rotary evaporator
  7. customthe aqueous suspension obtained
  8. temperaturewas cooled
  9. filtrationfiltered
  10. washThe filter residue was washed with water
  11. customdried

Sources & evidence

ORD record
ord-f18c67727dae4320803f6378b9324fea
Source dataset
uspto-grants-1989_09
Patent number
US04863920

Reaction notes

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