Water → HCID 13825885, compound

HRID 1654839Notes

Reaction equation

HRID 1654839 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[NH2:10][C:11]1[C:16]([OH:17])=[CH:15][CH:14]=[CH:13][N:12]=1.O>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:10][C:11]1[C:16]([O:17][CH2:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

7

Reactant 3

HCID 962WaterHCID 119062-Chlorobenzyl chlorideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 13825885HCID 13825885, compoundYield 50.7%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-chlorobenzyl chloride (47.6 g, 0.296 mol) and 2-amino-3-hydroxypyridine (29.6 g, 0.269 mol) in 40% aqueous sodium hydroxide solution (200 ml) and dichloromethane (200 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. A further 200 ml of water was added and the product extracted into dichloromethane, dried, the solvent evaporated and the residue triturated with petroleum ether to obtain the product (32 g, 46%), m.p. 95°-100° C.

Workup

  1. extractionthe product extracted into dichloromethane
  2. customdried
  3. customthe solvent evaporated
  4. customthe residue triturated with petroleum ether

Sources & evidence

ORD record
ord-14b63182e9ae47678c1e28188f55b30d
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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