Acetic Acid → 2-(4-Fluoro-benzyloxy)-5-((E)-2-nitro-vinyl)-pyridine

HRID 640223Notes

Reaction equation

C(O)(=O)C.[F:5][C:6]1[CH:21]=[CH:20][C:9]([CH2:10][O:11][C:12]2[N:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[F:5][C:6]1[CH:21]=[CH:20][C:9]([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15](/[CH:18]=[CH:25]/[N+:22]([O-:24])=[O:23])=[CH:16][N:17]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 105 °C

Procedure

To an acetic acid (20.0 mL) solution of 6-(4-fluoro-benzyloxy)-pyridine-3-carbaldehyde (2.23 g, 9.64 mmol) described in Manufacturing Example 58-1-2 were added nitromethane (2.94 g, 48.2 mmol) and ammonium acetate (1.49 g, 19.3 mmol) under nitrogen atmosphere, which was stirred for 2.5 hours at 105° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. This organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated from the filtrate under a reduced pressure to obtain the title compound (2.60 g) as a crude product.

Workup

extractionthe organic layer was extracted with ethyl acetate
washThis organic layer was washed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated from the filtrate under a reduced pressure

Sources & evidence

ORD record: ord-2a4e84792ca245f79f4692b82b80af06
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691882B2

Reaction notes

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