Water → 2-Amino-3-(2,6-dichlorobenzyloxy)pyridine

HRID 1654831Notes

Reaction equation

HRID 1654831 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4]Br.[NH2:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1.O>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:11][C:12]1[C:17]([O:18][CH2:4][C:3]2[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:10])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 301591-Bromomethyl-2,6-dichlorobenzene

Product 1

HCID 103783682-Amino-3-(2,6-dichlorobenzyloxy)pyridineYield 84.3%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,6-dichlorobenzyl bromide (50 g, 0.209 mol) and 2-amino-3hydroxypyridine (20.9 g, 0.19 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 yield a solid (43.1 g, 76%), m.p. 141°-142° C.

Workup

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

Sources & evidence

ORD record
ord-67e263ad91c14fcdb278f82aa57cfc06
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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