Hydrochloric Acid → HCID 21249960, compound

HRID 1531653Notes

Reaction equation

HRID 1531653 reaction equation
Cl.[BH4-].[Na+].[Br:4][C:5]1[C:6]([O:26][CH3:27])=[CH:7][C:8]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[N:13][N:12]=[C:11]([CH3:24])[CH2:10][C:9]=2[CH:25]=1>CO.O>[Br:4][C:5]1[C:6]([O:26][CH3:27])=[CH:7][C:8]2[C:14]([C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[N:13][NH:12][CH:11]([CH3:24])[CH2:10][C:9]=2[CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 21249973HCID 21249973, compound

Product 1

HCID 21249960HCID 21249960, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3.5 ml (43.2 mmol) of concentrated hydrochloric acid is first added, and then over about 10 minutes, 1.80 g (47.5 mmol) of sodium borohydride is added in portions to a suspension of 1.4 g (3.6 mmol) of 7-bromo-4-methyl-8-methoxy-1-(4-nitrophenyl)-5H-2,3-benzodiazepine (Example 3, Step C) in 60 ml of methanol. The suspension is stirred for another hour, and then diluted with water (60 ml). The crystalline material is suctioned off and washed with 50% aqueous methanol (3×50 ml). The 7-bromo-4-methyl-8-methoxy-1-(4-nitrophenyl)-4,5-dihydro-3H-2,3-benzodiazepine that is obtained as a crude product is further purified by suspension in 8 ml of hot ethanol. After suctioning-off, 1.23 g (88%) of chrome yellow crystals with a melting point of 172-174° C. is obtained.

Workup

  1. washwashed with 50% aqueous methanol (3×50 ml)

Sources & evidence

ORD record
ord-d3cd79cfa23c4dbaabf64448cfb7e33c
Source dataset
uspto-grants-2001_03
Patent number
US06200970B1

Reaction notes

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