Hydrochloric Acid → Methyl 6-methyl-3-nitro-2-oxo-4-phenoxy-1,2-dihydropyridine-1-acetate

HRID 1069439Notes

Reaction equation

[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:10][C:11]1[N:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:15](=[O:22])[C:14]([N+:23]([O-:25])=[O:24])=[C:13](OS(C(F)(F)F)(=O)=O)[CH:12]=1.Cl>O1CCCC1>[CH3:10][C:11]1[N:16]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[C:15](=[O:22])[C:14]([N+:23]([O-:25])=[O:24])=[C:13]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=1

Participants

Conditions

Temperature: -70 °C

Procedure

1.38 g (14.7 mmol) of phenol in solution in 20 ml of tetrahydrofuran are added dropwise to a suspension of 0.58 g (14.5 mmol) of sodium hydride in tetrahydrofuran. The mixture is left for 0.5 hour at room temperature, it is cooled to −70° C. and 5.24 g (14 mmol) of methyl 6-methyl-3-nitro-2-oxo-4-[[(tri fluoromethyl)sulphonyl]oxy]-1,2-dihydropyridine-1-acetate in solution in 20 ml of tetrahydrofuran are added dropwise. The temperature of the reaction medium is allowed to return to 0° C. and the medium is stirred at this temperature for 1 hour. The mixture is poured over 20 ml of a 1 N aqueous hydrochloric acid solution and extracted with twice 200 ml of dichloromethane. The medium is washed with 100 ml of a saturated sodium chloride solution, dried over magnesium sulphate and evaporated. The product is recrystallized from methanol.

Workup

customto return to 0° C.
extractionextracted with twice 200 ml of dichloromethane
washThe medium is washed with 100 ml of a saturated sodium chloride solution
dry with materialdried over magnesium sulphate
customevaporated
customThe product is recrystallized from methanol

Sources & evidence

ORD record: ord-62fed16900f44798b765bba9818102f3
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06252082B1

Reaction notes

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