Acetone, oxime → HCID 58928285, compound

HRID 852090

Reaction equation

HRID 852090 reaction equation
CC(=[N:4][OH:5])C.CC(C)([O-])C.[K+].Cl[C:13]1[C:18]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=2)=O)=[CH:17][CH:16]=[CH:15][N:14]=1>CN(C)C=O>[CH3:28][O:27][C:23]1[CH:22]=[C:21]([C:19]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[O:5][N:4]=2)[CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 67180Acetone, oximeHCID 10243711(2-Chloro-pyridin-3-yl)-(3-methoxy-phenyl)-methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 58928285HCID 58928285, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Combine acetone oxime (3.1 g, 42.4 mmol) in dimethylformamide (15 mL) and add potassium t-butoxide (4.76 g, 42.4 mmol) and stir for 1 hour. Add (2-chloro-pyridin-3-yl)-(3-methoxy-phenyl)-methanone (8.40 g, 34 mmol) dissolved in dimethylformamide (10 mL) and stir at room temperature, overnight. Separate the product between water and ether and evaporate. Purify by column (silica) chromatography (10% ethyl acetate/dichloromethane) and then reflux in a mixture of 1:1 ethanol:5% aqueous hydrochloric acid. Work-up with 5% aqueous sodium hydroxide and ether and purify by flash chromatography (5% ethyl acetate in dichloromethane) to give the title compound (5.21 g, 68% Yield).

Workup

  1. stirringstir at room temperature, overnight
  2. customSeparate the product between water and ether
  3. customevaporate
  4. customPurify by column (silica) chromatography (10% ethyl acetate/dichloromethane)
  5. temperaturereflux in a mixture of 1:1 ethanol
  6. custompurify by flash chromatography (5% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-56ca29a7da0b451cac9253a580723fd2
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Linked notes

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