N-(1-hydroxy-2,2,2-trichloroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide → N-(2,2-dichlorovinyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250498Notes

Reaction equation

O[CH:2]([NH:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[N:11]=1)=[O:9])[C:3](Cl)([Cl:5])[Cl:4]>C(O)(=O)C.C(OCC)(=O)C.O.[Zn]>[Cl:5][C:3]([Cl:4])=[CH:2][NH:7][C:8]([C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:28])[F:27])[CH:20]=2)[N:11]=1)=[O:9]

Participants

Conditions

Temperature: 50 °C

Procedure

1.0 g (0.0022 mol) of N-(1-hydroxy-2,2,2-trichloroethyl)-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide was dissolved in about 10 ml of acetic acid. The obtained solution was mixed with 0.29 g (0.0022×2.0 mol) of zinc dust and stirred at about 50° C. for about 5 hours. The reaction solution was distributed in ethyl acetate-water and washed with saturated sodium bicarbonate water and saturated brine. The organic phase of the solution was dried with anhydrous sodium sulfate, concentrated and purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

washwashed with saturated sodium bicarbonate water and saturated brine
dry with materialThe organic phase of the solution was dried with anhydrous sodium sulfate
concentrationconcentrated
custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record: ord-68fb9a2aeeb14befa1536fac4a6208b6
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06339045B1

Reaction notes

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