Potassium Hydroxide → 3-(4-Ethyl-2-methoxyphenoxy)-2-nitropyridine

HRID 1023915Notes

Reaction equation

F[C:2]1[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:11]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([O:20][CH3:21])[CH:14]=1)[CH3:12].[OH-].[K+]>C(#N)C>[CH2:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[C:3]([N+:8]([O-:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)=[C:15]([O:20][CH3:21])[CH:14]=1)[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 3-Fluoro 2-nitro pyridine (1.6 g, 0.01126 mol) in dry Acetonitrile (20 ml) was added 4-Ethyl-2-methoxy phenol (1.71 g, 11.3 mmol) in dry acetonitrile (10 ml) followed by potassium hydroxide (0.696 g, 12.4 mmol). The reaction mixture was heated to 80° C. and maintained for 2 hours. The solvent was evaporated and taken in ethyl acetate (200 ml). The organic layer was washed with water followed by brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2.6 g of crude product purified by column chromatography (5% Ethyl acetate in Petroleum ether) to yield: 1.75 g (56%) of title compound.

Workup

temperaturemaintained for 2 hours
customThe solvent was evaporated
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-395ef71bf7e946df920cb38a28fc34cd
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722746B2

Reaction notes

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