2-Amino-3-Hydroxypyridine → 3-[(4-Fluorophenyl)methoxy]pyridin-2-amine

HRID 1654822Notes

Reaction equation

HRID 1654822 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[NH2:10][C:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=1>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:10][C:11]1[C:16]([O:17][CH2:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 680214-Fluorobenzyl bromide

Product 1

HCID 27283773-[(4-Fluorophenyl)methoxy]pyridin-2-amine

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-fluorobenzyl bromide (75 g, 0.396 mol) and 2-amino-3-hydroxypyridine (39.6 g, 0.36 mol) in 40% aqueous sodium hydroxide solution (250 ml) and dichloromethane (250 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. The aqueous layer was extracted with dichloromethane and the combined organic layers washed with water, dried and evaporated. Chromatography (silica gel, chloroform) gave the product as an oil which later solidified (45.4 g, 49%), m.p. 96°-98° C.

Workup

  1. extractionThe aqueous layer was extracted with dichloromethane
  2. washthe combined organic layers washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-9b9cfb3ff04544aea650dd30b7ba810f
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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