Acetic Acid → 2-(3-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine

HRID 1891791Notes

Reaction equation

C(O)(=O)C.[F:5][C:6]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:11]=[CH:10][C:7]=1[CH:8]=O.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[F:5][C:6]1[CH:13]=[C:12]([CH:11]=[CH:10][C:7]=1/[CH:8]=[CH:25]/[N+:22]([O-:24])=[O:23])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To an acetic acid (15.0 mL) solution of 2-fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde (1.07 g, 4.63 mmol) described in Manufacturing Example 95-1-1 were added nitromethane (1.41 g, 23.2 mmol) and ammonium acetate (714 mg, 9.26 mmol) under nitrogen atmosphere at room temperature, which was stirred for 2 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (1.20 g) as a crude product.

Workup

extractionthe organic layer was extracted with ethyl acetate
washThe organic layer was washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record: ord-f94b5e876d0f4daf98beab99311624f6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507530B2

Reaction notes

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