Water → 2-Amino-3-(2-bromobenzyloxy)pyridine

HRID 1654841Notes

Reaction equation

HRID 1654841 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[NH2:10][C:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=1.O>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:10][C:11]1[C:16]([O:17][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Br:1])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 769652-Bromobenzyl bromide

Product 1

HCID 104688082-Amino-3-(2-bromobenzyloxy)pyridineYield 70.5%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-bromobenzyl bromide (50 g, 0.20 mol) and 2-amino-3-hydroxypyridine (20.0 g, 0.18 mol) in 40% aqueous sodium hydroxide solution (200 ml) and dichloromethane (200 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. A further 200 ml of water was added and the product extracted into dichloromethane, dried, and the solvent evaporated to obtain the product (35.4 g, 63%), m.p. 99°-100° C.

Workup

  1. extractionthe product extracted into dichloromethane
  2. customdried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-aebab68e8d2f4badb329a4194b71af3b
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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