Water → 2-Amino-3-(2-chloro-4,5-methylenedioxybenzyloxy)-pyridine

HRID 1654837

Reaction equation

HRID 1654837 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:9]1[O:13][C:12]2[CH:14]=[C:15]([Cl:20])[C:16]([CH2:18]Cl)=[CH:17][C:11]=2[O:10]1.O>ClCCl.[OH-].[Na+].CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:1][C:2]1[C:7]([O:8][CH2:18][C:16]2[CH:17]=[C:11]3[O:10][CH2:9][O:13][C:12]3=[CH:14][C:15]=2[Cl:20])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 901136-Chloropiperonyl chloride

Product 1

HCID 200770492-Amino-3-(2-chloro-4,5-methylenedioxybenzyloxy)-pyridineYield 24.3%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-amino-3-hydroxypyridine (9.75 g, 0.0886 mol) in dichloromethane (55 ml) and 40% sodium hydroxide (55 ml) was added Adogen 464 (5 ml) and 6-chloropiperonyl chloride (20 g, 0,0975 mol) with vigorous stirring. The mixture was stirred at room temperature for 16 hours. Water (55 ml) was added and the mixture extracted with dichloromethane. The combined organic layers were dried and evaporated, and the residue purified by flash chromatography (silica, 1% methanol/dichloromethane) and trituration with ether to yield the title compound (6 g), m.p. 100°-104° C.

Workup

  1. extractionthe mixture extracted with dichloromethane
  2. customThe combined organic layers were dried
  3. customevaporated
  4. customthe residue purified by flash chromatography (silica, 1% methanol/dichloromethane) and trituration with ether

Sources & evidence

ORD record
ord-c18b5067f4074f708abea2967a7af022
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Linked notes

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