4-Desoxypyridoxine hydrochloride → 3-(5-Hydroxymethyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile

HRID 1158939Notes

Reaction equation

HRID 1158939 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]([CH3:10])[C:3]=1[OH:11].Cl.Br[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=1>>[OH:9][CH2:8][C:7]1[C:2]([CH3:1])=[C:3]([O:11][CH2:14][C:15]2[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=2)[C:21]#[N:22])[C:4]([CH3:10])=[N:5][CH:6]=1

Participants

3

Reactant 2

HCID 674174-Desoxypyridoxine hydrochlorideHCID 97249Benzonitrile, 3-(bromomethyl)-

Product 1

HCID 586368033-(5-Hydroxymethyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrileYield 53%

Procedure

The coupling of 4-deoxypyridoxine hydrochloride (5.0 g, 0.026 mol) and α-bromo-m-tolunitrile (5.2 g, 0.026 mol), as described in Example 3, gave 3-(5-hydroxymethyl-2,4-dimethyl-pyridin-3-yloxymethyl)-benzonitrile (26) (3.7 g, 52% yield).

Sources & evidence

ORD record
ord-5cc9ad2332284aa4989d6bff0f17dc8d
Source dataset
uspto-grants-2010_10
Patent number
US07812037B2

Reaction notes

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