Dichloromethane → 2-Amino-3-(2-chloro-6-fluorobenzyloxy)-6-methylpyridine

HRID 1654930Notes

Reaction equation

HRID 1654930 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.ClCCl.[OH-].[Na+].[Cl:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:17]=1[CH2:18]Cl>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:1][C:2]1[C:7]([O:8][CH2:18][C:17]2[C:20]([F:24])=[CH:21][CH:22]=[CH:23][C:16]=2[Cl:15])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 885002-Amino-6-methylpyridin-3-olHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzene

Product 1

HCID 200769742-Amino-3-(2-chloro-6-fluorobenzyloxy)-6-methylpyridine

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-hydroxy-6-methylpyridine (4.3 g, 0.035 mol), dichloromethane (26 ml) and 40% aqueous sodium hydroxide solution (26 ml) was stirred for five minutes at room temperature, then 2-chloro-6-fluorobenzyl chloride (6.8 g, 0.038 mol) and Adogen 464 (2.5 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 ethanol gave the desired product. Yield 6.3 g (67%), m.p. 108°-109 ° C.

Workup

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

Sources & evidence

ORD record
ord-c73661605cef49ffab5025d851406823
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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