2-(2-Chloropyridin-4-yl)-1-(4-fluorophenyl)ethanone → 1-(2-Chloropyridin-4-yl)-2-(4-fluorophenyl)ethane-1,2-dione-1-oxime

HRID 730044Notes

Reaction equation

[N:1]([O-:3])=O.[Na+].[Cl:5][C:6]1[CH:11]=[C:10]([CH2:12][C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:14])[CH:9]=[CH:8][N:7]=1>O.C(O)(=O)C>[Cl:5][C:6]1[CH:11]=[C:10]([C:12](=[N:1][OH:3])[C:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[O:14])[CH:9]=[CH:8][N:7]=1

Participants

Conditions

Temperature: 10 °C

Procedure

With stirring and cooling in a water bath (about 10° C.), a solution of NaNO2 (0.85 g; 12.3 mmol) in H2O (10 ml) was added dropwise over a period of 2.5 min to a solution of 21a (3.0 g; 12 mmol) in glacial acetic acid. After the addition had ended, the reaction mixture was stirred at room temperature for 0.5 h, H2O (60 ml) was added and stirring at room temperature was continued for 3 h. The light-beige precipitate was filtered off, washed with water and dried under reduced pressure over CaCl2.

Workup

additionAfter the addition
stirringthe reaction mixture was stirred at room temperature for 0.5 h
stirringstirring at room temperature
filtrationThe light-beige precipitate was filtered off
washwashed with water
dry with materialdried under reduced pressure over CaCl2

Sources & evidence

ORD record: ord-d8dfd1f5a8f043eaa55f81b7b241d6ed
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582660B2

Reaction notes

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