Pyridine → 4-(2,1-Benzisoxazolyl)methylpyridinium bromide

HRID 648453Notes

Reaction equation

HRID 648453 reaction equation
[Br:1]C[C:3]1[C:8]2=[CH:9][O:10][N:11]=[C:7]2[CH:6]=[CH:5][CH:4]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH3:18]COCC>>[Br-:1].[N:11]1[O:10][C:9]([CH2:18][C:15]2[CH:16]=[CH:17][NH+:12]=[CH:13][CH:14]=2)=[C:8]2[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=12

Participants

4

Reactant 3

HCID 1049PyridineHCID 3283Diethyl EtherHCID 14098280HCID 14098280, compound

Product 1

HCID 201449394-(2,1-Benzisoxazolyl)methylpyridinium bromideYield 66%

Procedure

To a solution of 3.99 g (18.8 mmoles) (2) in 30 ml ether under nitrogen was added 1.49 g (18.8 mmoles) pyridine. A white precipitate formed and the mixture was stirred overnight. The precipitate was then filtered off, washed with ether, and dried to give 3.64 g (66%) 4-(2,1-benzisoxazolyl)methylpyridinium bromide, m.p. 172°-174°; nmr (DMSO-d6): 6.3 (s, 2H), 7.5 (m, 3H), 8.2 (m, 2H), 8.9 (m, 1H), 9.6 (dd, 2H), 10.3 (s, 1H).

Workup

  1. customA white precipitate formed
  2. filtrationThe precipitate was then filtered off
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-6418c191b14f477881366ea5f092e816
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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