Water → HCID 10265056, compound

HRID 1654855Notes

Reaction equation

HRID 1654855 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Br.[NH2:11][C:12]1[C:17]([OH:18])=[CH:16][CH:15]=[CH:14][N:13]=1.O>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:11][C:12]1[C:17]([O:18][CH2:4][C:3]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

7

Reactant 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 109883732,4-Dichlorobenzyl bromide

Product 1

HCID 10265056HCID 10265056, compound

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,4-dichlorobenzyl bromide (15 g, 76.7 mmol) and 2-amino-3hydroxypyridine (7.7 g, 69.7 mmol) in 40% aqueous sodium hydroxide solution (52 ml) and dichloromethane (52 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. More water was added and the product extracted into dichloromethane, dried, and the solvent evaporated to obtain the product after trituration with ether (13.3 g, 70%), m.p. 120°-121° C.

Workup

  1. extractionthe product extracted into dichloromethane
  2. customdried
  3. customthe solvent evaporated
  4. customto obtain the product after trituration with ether (13.3 g, 70%), m.p. 120°-121° C.

Sources & evidence

ORD record
ord-313baf94142846ef921a4ad8d7bcb0a9
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

Loading…