Dichloromethane → HCID 20076935, compound

HRID 1654877Notes

Reaction equation

HRID 1654877 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.ClCCl.[OH-].[Na+].[CH3:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].O>[NH2:1][C:2]1[C:7]([O:8][CH2:14][C:15]2[CH:22]=[CH:21][C:18]([CH3:19])=[CH:17][CH:16]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7721p-Xylyl bromideHCID 14798Sodium HydroxideHCID 281142-Amino-3-Hydroxypyridine

Product 1

HCID 20076935HCID 20076935, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-hydroxypyridine (2.7 g, 0.024 mol), dichloromethane (40 ml) and 40% aqueous sodium hydroxide solution (40 ml) was stirred for 5 rains, then 4methylbenzyl bromide (4.51 g, 0.024 mol) and Adogen 464 (3 ml) were added and stirring was continued for 16 hours. The mixture was diluted with water and extracted with dichloromethane (×2), and the combined organic layers dried, evaporated, and triturated with ether. Yield 2.92 g (56%), m.p. 123° 125 ° C.

Workup

  1. stirringstirring
  2. extractionextracted with dichloromethane (×2)
  3. customthe combined organic layers dried
  4. customevaporated
  5. customtriturated with ether
  6. customYield 2.92 g (56%), m.p. 123° 125 ° C.

Sources & evidence

ORD record
ord-f25d9d38e2e248cc83b1233564d71422
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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