Sodium borohydride → 1-[(1,2,3,4-Tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-4-anilino isonipecotonitrile

HRID 2072483Notes

Reaction equation

HRID 2072483 reaction equation
Cl.[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:21][CH2:20][C:17]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:18]#[N:19])[CH2:16][CH2:15]1.[BH4-].[Na+]>CO.O>[OH:2][CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH:4]1[CH2:13][N:14]1[CH2:21][CH2:20][C:17]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:18]#[N:19])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 1317109081-[(1,2,3,4-Tetrahydro-1-oxo-2-naphthalenyl)-methyl]-4-anilino isonipecotonitrile, hydrochloride

Product 1

HCID 543671651-[(1,2,3,4-Tetrahydro-1-hydroxy-2-naphthalenyl)methyl]-4-anilino isonipecotonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Finely-ground 1-[(1,2,3,4-tetrahydro-1-oxo-2-naphthalenyl)-methyl]-4-anilino isonipecotonitrile, hydrochloride (1:1) (5.0 g) is slurried in methanol (100 ml) and cooled in ice. To this mixture is added an aqueous solution of sodium borohydride (3.0 g) in water (25 ml). The resulting mixture is stirred for 15 hours at room temperature under nitrogen. Dilution of the reaction mixture mixture with water (200 ml), extraction with methylene chloride, and concentration of the dried organic solution give the title compound.

Workup

  1. temperaturecooled in ice
  2. extractionDilution of the reaction mixture mixture with water (200 ml), extraction with methylene chloride, and concentration of the dried organic solution

Sources & evidence

ORD record
ord-89b5ebcede5f44dd819b68739d8e72c0
Source dataset
uspto-grants-1977_09
Patent number
US04051248

Reaction notes

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