2-Amino-3-Hydroxypyridine → 3-[(4-Methoxybenzyl)oxy]pyridin-2-amine

HRID 1654826Notes

Reaction equation

HRID 1654826 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[NH2:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:11][C:12]1[C:17]([O:18][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 2

HCID 281142-Amino-3-HydroxypyridineHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 27283893-[(4-Methoxybenzyl)oxy]pyridin-2-amineYield 76.7%

Reagents, catalysts & solvents 4

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 4-methoxybenzyl bromide (25 g, 0.159 mol) and 2-amino-3-hydroxypyridine (15.9 g, 0.145 mol) in 40% aqueous sodium hydroxide solution (150 ml) and dichloromethane (150 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. The mixture was diluted with further water and dichloromethane, the product extracted into dichloromethane, and the combined organic layers washed with water, dried and evaporated. The resulting solid was washed with ether to yield the product (25.6 g, 70%)

Workup

  1. extractionthe product extracted into dichloromethane
  2. washthe combined organic layers washed with water
  3. customdried
  4. customevaporated
  5. washThe resulting solid was washed with ether

Sources & evidence

ORD record
ord-c45126958ef04d6a85f2ce607e71d9cf
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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