4-Methylpyridine → 1-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanone

HRID 1809140Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[N:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.[Cl:16][C:17]1[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=1[C:19](N(OC)C)=[O:20]>C1COCC1>[Cl:16][C:17]1[CH:28]=[CH:27][CH:26]=[CH:25][C:18]=1[C:19](=[O:20])[CH2:15][C:12]1[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To lithium diisopropyl amide (6.5 mL, 1.6 M in cyclohexane, 10.4 mmol) in THF (20.0 mL) at −78° C. was added a solution of 4-picoline (1.07 g mL, 11.5 mmol) in THF (10.0 mL) dropwise. The dry ice bath was removed. The reaction mixture was stirred at 0° C. for 30 minutes, and cooled back to −78° C. A solution of 2-chloro-N-methoxy-N-methylbenzamide (21) (2.39 g, 12 mmol) in THF (10.0 mL) was added dropwise. The reaction mixture was warmed to room temperature and stirred overnight. White solid was filtered off and dissolved in ethyl acetate. The organic phase was washed with water, brine, dried over dried magnesium sulfate and concentrated under vacuum to give 1-(2-chlorophenyl)-2-(pyridin-4-yl)ethanone (22) (1.09 g, 4.7 mmol, 47%) as white solid.

Workup

customThe dry ice bath was removed
temperaturecooled back to −78° C
temperatureThe reaction mixture was warmed to room temperature
stirringstirred overnight
filtrationWhite solid was filtered off
dissolutiondissolved in ethyl acetate
washThe organic phase was washed with water, brine
dry with materialdried over dried magnesium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-f77246bc123d4cf69ae8c98f0bdeb934
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362022B2

Reaction notes

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