Dichloromethane → HCID 10082660, compound

HRID 1654922Notes

Reaction equation

HRID 1654922 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.ClCCl.[OH-].[Na+].[F:14][C:15]1[C:22]([CH3:23])=[CH:21][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][CH:21]=[C:22]([CH3:23])[C:15]=2[F:14])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 281142-Amino-3-HydroxypyridineHCID 519062Benzene, 1-(bromomethyl)-2-fluoro-3-methyl-

Product 1

HCID 10082660HCID 10082660, compound

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-amino-3-hydroxypyridine (2.8 g, 0.026 mol), dichloromethane (20 ml) and 40% aqueous sodium hydroxide solution (20 ml) was stirred for five minutes, then 2-fluoro-3-methylbenzyl bromide (5.0 g, 0.026 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 3.99 g (66%), m.p. 115°-118 ° 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-2329a15a3eaa4c0a94fff01766267128
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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