Methanol → HCID 70509492, compound

HRID 543713Notes

Reaction equation

HRID 543713 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]2=3)=[O:8])=[CH:3][CH:2]=1.[BH4-].[Na+].[CH3:27]O>>[OH2:8].[CH3:27][N:1]1[CH2:2][CH2:3][C:4]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]2=3)=[O:8])=[CH:5][CH2:6]1.[CH3:27][N:1]1[CH2:2][CH2:3][C:4]([C:7]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]3[CH:21]=[CH:22][CH:23]=[CH:24][C:10]2=3)=[O:8])=[CH:5][CH2:6]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 13285860HCID 13285860, compound

Product 1

HCID 70509492HCID 70509492, compound

Procedure

2.3 g (0.005 mol) of 5,10-dihydro-5-[(4-pyridinyl)carbonyl]-11H-dibenzo[b,e][1,4]diazepin-11-one methoiodide were suspended in 200 ml of methanol and at 0° C. 0.25 g (0.006 mol) of sodium borohydride were added in batches. The mixture was stirred for a further hour in the ice bath. It was then stirred into 1 liter of ice-cold water and extracted exhaustively with methylene chloride. The combined extracts were washed with water, dried over sodium sulphate and concentrated by evaporation in vacuo. After recrystallization from diisopropylether/methanol, the colorless crystals melted at 233°-234° C.

Workup

  1. extractionextracted exhaustively with methylene chloride
  2. washThe combined extracts were washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation in vacuo
  5. customAfter recrystallization from diisopropylether/methanol

Sources & evidence

ORD record
ord-edc0b0b44d7d4f25bcd6e6a622b49d71
Source dataset
uspto-grants-1984_05
Patent number
US04447434

Reaction notes

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