Water → HCID 9993203, compound

HRID 1654857Notes

Reaction equation

HRID 1654857 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[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]=[C:7]([Cl:10])[CH:8]=[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 34957442,5-Dichlorobenzyl bromide

Product 1

HCID 9993203HCID 9993203, compound

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2,5-dichlorobenzyl bromide (14.8 g, 75.9 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 (8.6 g, 46%), m.p. 103°-104 ° C.

Workup

  1. extractionthe product extracted into dichloromethane
  2. customdried
  3. customthe solvent evaporated
  4. customto obtain the product after trituration with ether (8.6 g, 46%), m.p. 103°-104 ° C.

Sources & evidence

ORD record
ord-227236f6745a43918fc0164cb9bc1895
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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