Methanol → HCID 13269697, compound

HRID 2295284Notes

Reaction equation

HRID 2295284 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]=[N:24][C:10]2=3)=[O:8])=[CH:3][CH:2]=1.[BH4-].[Na+].[CH3:27]O>>[CH3:27][N:1]1[CH2:6][CH2:5][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]=[N:24][C:10]2=3)=[O:8])=[CH:3][CH2:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 13269698HCID 13269698, compound

Product 1

HCID 13269697HCID 13269697, compound

Procedure

A quantity of 2.3 gm (0.005 mol) of 5,11-dihydro-11-[(4-pyridinyl)-carbonyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one methoiodide was suspended in 200 ml of methanol, and at 0° C. 0.25 gm (0.006 mol) of sodium borohydride were added thereto in portions. The resulting mixture was stirred for a further hour in an ice bath. Then, the mixture was 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 being recrystallized from diisopropyl ether/methanol, the colorless crystals melted at 226°-227° C.

Workup

  1. customat 0° C
  2. extractionextracted exhaustively with methylene chloride
  3. washThe combined extracts were washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation in vacuo
  6. customAfter being recrystallized from diisopropyl ether/methanol

Sources & evidence

ORD record
ord-3f944770277f4ed79f99480d525302a5
Source dataset
uspto-grants-1984_01
Patent number
US04424226

Reaction notes

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