Water → HCID 22903522, compound

HRID 1440256Notes

Reaction equation

HRID 1440256 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][C:7](=[O:30])[C:6]=2[CH:31]=1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([C:12](=[O:29])[C:13]3[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:28])[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH3:27])=[N:15][CH:14]=3)[CH2:10][CH2:9][CH2:8][CH:7]([OH:30])[C:6]=2[CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 229035137-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine

Product 1

HCID 22903522HCID 22903522, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 7-chloro-5-oxo-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.3 g) in methanol (5 ml) is added with stirring sodium borohydride (0.05 g) under ice-cooling, and the mixture is stirred at room temperature for one hour. To the reaction solution is added water, and the mixture is extracted with dichloromethane. The extract is washed with water, and dried over magnesium sulfate. The resultant is evaporated under reduced pressure to remove the solvent, and the residue is purified by silica gel column chromatography to give 7-chloro-5-hydroxy-1-[6-(2-methylbenzoylamino)nicotinoyl]-2,3,4,5-tetrahydro-1H-benzazepine (0.2 g) as colorless amorphous.

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with dichloromethane
  3. washThe extract is washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe resultant is evaporated under reduced pressure
  6. customto remove the solvent
  7. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e107d16468dd4355ada68a1a981819bb
Source dataset
uspto-grants-1996_03
Patent number
US05498609

Reaction notes

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