Water → 3-(2-Trifluoromethyl-benzyloxy)-pyridin-2-ylamine

HRID 1654845Notes

Reaction equation

HRID 1654845 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH2:5]Cl.[NH2:13][C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=1.O>[OH-].[Na+].ClCCl.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[NH2:13][C:14]1[C:19]([O:20][CH2:5][C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[C:2]([F:12])([F:11])[F:1])=[CH:18][CH:17]=[CH:16][N:15]=1

Participants

7

Reactant 3

HCID 962WaterHCID 281142-Amino-3-HydroxypyridineHCID 890281-(Chloromethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 143684023-(2-Trifluoromethyl-benzyloxy)-pyridin-2-ylamineYield 72.5%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 2-trifluoromethylbenzyl chloride (50 g, 0.257 mol) and 2-amino-3hydroxypyridine (25.2 g, 0.233 mol) in 40% aqueous sodium hydroxide solution (200 ml) and dichloromethane (200 ml) was treated with Adogen 464 (5 ml) and stirred vigorously at room temperature for 16 hours. A further 200 ml of water was added and the product extracted into dichloromethane, dried, and the solvent evaporated to obtain the product (45.3 g, 66%), m.p. 105°-110° C.

Workup

  1. extractionthe product extracted into dichloromethane
  2. customdried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-b8df26b004574a90b0028dcadb967c0b
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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