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

HRID 1654847Notes

Reaction equation

HRID 1654847 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[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[F:1])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 3

HCID 962WaterHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 102424912-Amino-3-(2-fluorobenzyloxy)pyridineYield 80%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-fluorobenzyl chloride (50 g, 0.346 mol) and 2-amino-3-hydroxypyridine (39 g, 0.3 15 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 (54.9 g, 80%), m.p. 85°-86° C.

Workup

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

Sources & evidence

ORD record
ord-4316c19f256640b8940604e2b0b2eff9
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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