Acetic Acid → 2-(2-Fluoro-4-((E)-2-nitro-vinyl)-phenoxymethyl)pyridine
Reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH:9]=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:7]=[C:8](/[CH:9]=[CH:25]/[N+:22]([O-:24])=[O:23])[CH:11]=[CH:12][C:13]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 110 °C
Procedure
To an acetic acid (25.0 mL) solution of 3-fluoro-4-(pyridin-2-ylmethoxy)-benzaldehyde (2.80 g, 12.1 mmol) described in Manufacturing Example 87-1-1 were added nitromethane (3.69 g, 60.5 mmol) and ammonium acetate (1.87 g, 24.2 mmol) under nitrogen atmosphere at room temperature, which was stirred for 2 hours at 110° 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 (3.00 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-2ba73fb87db94c37814d84991cc0c0df
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08153662B2
Reaction notes
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