Sodium hydride → 7-Chloro-4-(3-trifluoromethylpyridine-2-yl)oxymethylquinoline

HRID 1953452Notes

Reaction equation

HRID 1953452 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:13])=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:17]1[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=1>C1COCC1>[F:24][C:23]([F:26])([F:25])[C:22]1[C:17]([O:1][CH2:2][C:3]2[C:12]3[C:7](=[CH:8][C:9]([Cl:13])=[CH:10][CH:11]=3)[N:6]=[CH:5][CH:4]=2)=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 23298203(7-Chloroquinolin-4-yl)methanol

Product 1

HCID 232981957-Chloro-4-(3-trifluoromethylpyridine-2-yl)oxymethylquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxymethyl-7-chloroquinoline (0.6 g, 3.12 mmol) was dissolved with stirring in dry THF (20 mls) and sodium hydride (0.15 g, 60% dispersion in mineral oil, 3.75 mmol) added. The mixture was stirred at room temperature for one hour and 2-chloro-3-trifluoromethylpyridine (0.62 g, 3.42 mmol) added. The mixture was stirred overnight and worked up to provide the product (0.9 g, % as a tan solid, mp 125-7° C.

Workup

  1. stirringThe mixture was stirred overnight
  2. customto provide the product (0.9 g

Sources & evidence

ORD record
ord-f17d30380c6d476b9e07b56b148b7205
Source dataset
uspto-grants-2000_09
Patent number
US06117884

Reaction notes

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