Acetic Acid → (E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=O)=[CH:11][CH:10]=1.[N+:17]([CH3:20])([O-:19])=[O:18].C([O-])(=O)C.[NH4+].C(O)(=O)C>O.C(OCC)(=O)C>[N+:17](/[CH:20]=[CH:13]/[C:12]1[CH:15]=[CH:16][C:9]([CH2:8][O:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:10][CH:11]=1)([O-:19])=[O:18]Participants
7
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 4-(pyridin-2-yloxymethyl)-benzaldehyde (26.8 g, 126 mmol)) described in Manufacturing Example 1-2-2, nitromethane (34 mL, 630 mmol), ammonium acetate (19 g, 252 mmol), and acetic acid (90 mL) was stirred for 1 hour and 30 minutes at 100° C. Ethyl acetate and water were added thereto, which was separated. The organic layer was washed with water five times and saturated sodium bicarbonate water once, dried over anhydrous magnesium sulfate, and filtered. This filtrate was concentrated under a reduced pressure, so as to obtain a crude product of the title compound (31 g).
Workup
- customwhich was separated
- washThe organic layer was washed with water five times and saturated sodium bicarbonate water once
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationThis filtrate was concentrated under a reduced pressure
Sources & evidence
- ORD record
- ord-eebeadc1789046c4b1a7fd242c3c590f
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513287B2
Reaction notes
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