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

HRID 1654817Notes

Reaction equation

HRID 1654817 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH3:9].[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][CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=2[CH3:9])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

6

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 684723-Bromo-o-xylene

Product 1

HCID 138258823-[(2-Methylphenyl)methoxy]pyridin-2-amine

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of a -bromo-o-xylene (89.6 g, 0.48 mol) and 2-amino-3-hydroxypyridine (48 g, 0.436 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-fa4734aa57674d49aa86f79c0d6dd24b
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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