Dichloromethane → 2-Amino-3-(2,4-difluorobenzyloxy)pyridine

HRID 1654908Notes

Reaction equation

HRID 1654908 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.ClCCl.[OH-].[Na+].[F:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH2:17]Br>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:1][C:2]1[C:7]([O:8][CH2:17][C:16]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:15]=2[F:14])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 281142-Amino-3-HydroxypyridineHCID 902971-(Bromomethyl)-2,4-difluorobenzene

Product 1

HCID 100143212-Amino-3-(2,4-difluorobenzyloxy)pyridine

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-hydroxy pyridine (2.66 g, 0.024 mol), dichloromethane (20 ml) and 40% aqueous sodium hydroxide solution (20 ml) was stirred for five minutes, then 2,4-difluorobenzyl bromide (5.00g, 0.024 mol) and Adogen 464 (3 ml) were added and stirring continued for 16 hours. The mixture was diluted with water and extracted with dichloromethane. Drying and evaporation of the organic extracts, and trituration with ether gave the desired product. Yield 2.7 g (48%), m.p. 105°-107 ° C.

Workup

  1. stirringstirring
  2. waitcontinued for 16 hours
  3. extractionextracted with dichloromethane
  4. customDrying
  5. customevaporation of the organic extracts, and trituration with ether

Sources & evidence

ORD record
ord-418cbcdc073d42949af24e59adbffbe0
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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