Penta-1,3-diene → 2-(Bromomethyl)-6-phenylpyridine

HRID 27253Notes

Reaction equation

HRID 27253 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.C=CC=CC.[Br:19]N1C(=O)CCC1=O>>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1

Participants

4

Reactant 3

HCID 15301Penta-1,3-dieneHCID 67184N-bromobutanimideHCID 27628852-Methyl-6-phenylpyridine

Product 1

HCID 152294502-(Bromomethyl)-6-phenylpyridine

Procedure

2-Methyl-6-phenylpyridine, obtainable from 1,3-pentadiene and benzonitirle via the procedure of Janz and McColloch [J. Am. Chem. Soc., 77 (1955), 3413] is treated with N-bromosuccinimide to give 2-bromomethyl-6-phenylpyridine. The bromomethyl compound is treated with 1-methyl-2-cyanopyrrolidine, and the resulting salt is rearranged using sodium amide in liquid ammonia and decyanated with sodium borohydride in ethanol according to the procedures described in Example 1. The product can be purified by distillation.

Sources & evidence

ORD record
ord-b5b01ff0f8be46b89631ad692b7cb01f
Source dataset
uspto-grants-1980_09
Patent number
US04220781

Reaction notes

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