Methanol → HCID 13282024, compound

HRID 2295295Notes

Reaction equation

HRID 2295295 reaction equation
[C:1]([N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12](=[O:20])[C:11]2=[CH:21][S:22][CH:23]=[C:10]12)(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[H][H].[CH3:28]O>>[CH3:28][N:5]1[CH2:4][CH2:3][C:2]([C:1]([N:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:20])[C:11]3=[CH:21][S:22][CH:23]=[C:10]23)=[O:8])=[CH:7][CH2:6]1

Participants

5

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 13282025HCID 13282025, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13282024HCID 13282024, compoundYield 35%

Procedure

4,9-Dihydro-4-isonicotinoyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one methoiodide in an amount of 3.4 gm (0.0073 mol) was suspended in 40 ml of methanol, and at 0° C. 0.5 gm (0.014 mol) of sodium borohydride were added in portions. After the development of hydrogen ceased, the mixture was stirred for a further two hours in an ice bath. Then, 100 ml of ice-water was added, the mixture was filtered, and the filtrate was extracted with methylene chloride. The extraction residue was recrystallized from acetonitrile. 4,9-Dihydro-4-[(1-methyl-1,2,5,6-tetrahydro-4-pyridinyl)carbonyl]-10H-thieno[3,4-b][1,5]benzodiazepin-10-one was obtained, m.p.: 210°-212° C., in a yield of 35% of theory.

Workup

  1. customat 0° C
  2. filtrationthe mixture was filtered
  3. extractionthe filtrate was extracted with methylene chloride
  4. customThe extraction residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-65fd053294714d9c9e6f878a353d9a79
Source dataset
uspto-grants-1984_01
Patent number
US04424225

Reaction notes

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