Methyl iodide → N-Methyl-3-nitro-N-(3-pyridinylmethyl)benzamide

HRID 726283Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[C:7]([NH:9][CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([O-:3])=[O:2].[CH3:20]C(C)([O-])C.[K+].IC.C(=O)(O)[O-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[C:7]([N:9]([CH3:20])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:8])([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-nitro-N-(3-pyridylmethyl)benzamide (2.00 g) in tetrahydrofuran (40 ml) was added potassium tert-butoxide (917 mg) in one portion in an ice-cooled bath. The stirring was continued for 40 minutes and then iodomethane (0.53 ml) was added thereto. The reaction mixture was stirred at 0° C. for one hour, then at ambient temperature for five hours. Saturated sodium bicarbonate solution was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution. After dried over anhydrous magnesium sulfate and filtered, the solvent was removed in vacuo and the residue was purified by flash chromatography (methanol-chloroform 3%, V/V) to afford 3-nitro-N-methyl-N-(3-pyridylmethyl)benzamide (1.8 g) as a yellow oil.

Workup

temperaturecooled bath
waitat ambient temperature for five hours
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated sodium chloride solution
dry with materialAfter dried over anhydrous magnesium sulfate
filtrationfiltered
customthe solvent was removed in vacuo
customthe residue was purified by flash chromatography (methanol-chloroform 3%, V/V)

Sources & evidence

ORD record: ord-860d52d0baed48c8bd1793d53b3bbe22
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05708173

Reaction notes

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