Water → 3-(1-Phenylethoxy)pyridin-2-amine

HRID 1654849Notes

Reaction equation

HRID 1654849 reaction equation
Br[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[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][CH:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH3:3])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 3

HCID 962WaterHCID 11454(1-Bromoethyl)benzeneHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 127582763-(1-Phenylethoxy)pyridin-2-amineYield 65.2%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-bromoethylbenzene (55 g, 0.296 mol) and 2-amino-3-hydroxypyridine (29.6 g, 0.269 mol) in 40% aqueous sodium hydroxide solution (200 ml) and dichloromethane (200 ml) was treated with Adogen 464 (10 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. Chromatography (silica gel, chloroform-methanol) gave the product as a crystalline solid (37.6 g, 63%), m.p. 79°-83° C.

Workup

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

Sources & evidence

ORD record
ord-29b8992dc9cb45d2852b2d4474eb9d83
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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