Ethanol → 1-(4-Amino-2,6-difluorophenyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 1526384Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([F:11])[C:3]=1[N:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]#[N:21])[C:13]1=[O:22].[Cl-].[NH4+].C(O)C.C(=O)([O-])O.[Na+]>[Fe].O>[NH2:8][C:6]1[CH:5]=[C:4]([F:11])[C:3]([N:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]#[N:21])[C:13]2=[O:22])=[C:2]([F:1])[CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a mixture of 1-(2,6-difluoro-4-nitrophenyl)-4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile obtained in Step A (3.00 g), ammonium chloride (5.22 g), ethanol (48 mL) and water (12 mL) was added iron powder (2.18 g) at room temperature, and the reaction mixture was heated at 90° C. for 1 hr. The reaction mixture was cooled to room temperature, and slowly poured into saturated sodium hydrogen carbonate solution, and the mixture was extracted with a mixed solvent of tetrahydrofuran/ethyl acetate=3/1. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. To the residue was added isopropyl ether (10 mL), and the mixture was stirred for 15 min. The precipitate was collected by filtration to give the title compound (1.95 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionthe mixture was extracted with a mixed solvent of tetrahydrofuran/ethyl acetate=3/1
washThe extract was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
additionTo the residue was added isopropyl ether (10 mL)
filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record: ord-749fd7cb50ab4d5a91ca25a8ee52b440
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09085578B2

Reaction notes

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