Dichloromethane → HCID 12758273, compound

HRID 1654884Notes

Reaction equation

HRID 1654884 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:10][Cl:11].[OH-].[Na+].Cl[C:15]1[CH:22]=C[CH:20]=[CH:19][C:16]=1[CH2:17]Br>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:1][C:2]1[C:7]([O:8][CH2:17][C:16]2[CH:19]=[CH:20][C:10]([Cl:11])=[CH:22][CH:15]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11905alpha-Bromo-o-chlorotolueneHCID 14798Sodium HydroxideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 12758273HCID 12758273, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-hydroxy pyridine (3.45 g, 0.313 mol), dichloromethane (20 ml) and 40% aqueous sodium hydroxide solution (20 ml) was stirred for five minutes, then 2chlorobenzyl bromide (6.09 g, 0.0315 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 3.5 g (48%), m.p. 121°-123 ° 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-23eb50db7f2b45cd92f413edf74688d1
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

Loading…