Dichloromethane → 2-Amino-3-(3-chloro-2-fluorobenzyloxy)pyridine

HRID 1654919Notes

Reaction equation

HRID 1654919 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.ClCCl.[OH-].[Na+].[Cl:14][C:15]1[C:16]([F:23])=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:1][C:2]1[C:7]([O:8][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([Cl:14])[C:16]=2[F:23])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 281142-Amino-3-HydroxypyridineHCID 5228271-(Bromomethyl)-3-chloro-2-fluorobenzene

Product 1

HCID 103999912-Amino-3-(3-chloro-2-fluorobenzyloxy)pyridine

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-hydroxypyridine (2.42 g, 0.022 mol), dichloromethane (20 ml) and 40% aqueous sodium hydroxide solution (20 ml) was stirred for five minutes, then 3-chloro-2-fluorobenzyl bromide (5.0 g, 0.022 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 3.22 g (58%), m.p. 98°-100 ° 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-69713d3a9ea54bdbaf431e4f8bb14fa7
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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