Water → 3-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamine

HRID 1654833Notes

Reaction equation

HRID 1654833 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F: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]([F:1])=[CH:9][CH:8]=[CH:7][C:6]=2[F:10])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 5814352-(Bromomethyl)-1,3-difluorobenzene

Product 1

HCID 102634983-(2,6-Difluoro-benzyloxy)-pyridin-2-ylamineYield 71.2%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,6-difluorobenzyl bromide (25 g, 0.121 mol) and 2-amino-3hydroxypyridine (12.1 g, 0.11 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 (18.5 g, 65%), m.p. 124°-128° C.

Workup

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

Sources & evidence

ORD record
ord-6bf9cd4489bd429cb13346a7f372659f
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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