Hydrochloric Acid → 3-Methoxy-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

HRID 218504

Reaction equation

[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC(C)([O-])C.[K+].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=1[CH3:26].Cl>CS(C)=O.O>[CH3:1][O:2][C:3]1[C:4](=[O:9])[N:5]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:18]=2[CH3:26])[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

28.5 g (228 mol) of 3-methoxypyridin-2(1H)-one are dissolved in 850 ml of dimethyl sulfoxide and admixed at RT with 31 g (273 mmol) of potassium tert-butoxide. The suspension is stirred at RT for 30 min, before 35 g (228 mmol) of 1-fluoro-2-methyl-4-nitrobenzene are added, and the reaction solution is heated to 80° C. for 20 h. The mixture is then cautiously diluted with 1 l of water and brought to pH 1-2 with 1N hydrochloric acid. The solution is extracted repeatedly with dichloromethane. The combined organic extracts are washed with water and saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid is washed with a little tert-butyl methyl ether, filtered off and dried under reduced pressure. This affords 42.8 g (72% of theory) of the desired compound.

Workup

additionare added
extractionThe solution is extracted repeatedly with dichloromethane
washThe combined organic extracts are washed with water and saturated sodium chloride solution
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
washThe resulting solid is washed with a little tert-butyl methyl ether
filtrationfiltered off
customdried under reduced pressure

Sources & evidence

ORD record: ord-ff66636a79984f4390ae566357b10ac0
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198267B2

Linked notes

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