Acetic Acid → (E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine

HRID 1930753Notes

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

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(pyridin-2-yloxymethyl)-benzaldehyde (26.8 g, 26 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 to separate the reaction mixture. The organic layer was separated, 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 titled compound (31 g).

Workup

customto separate the reaction mixture
customThe organic layer was separated
washwashed 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-f8bbb5a0b17640ec85aad95ece5ef2fc
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188119B2

Reaction notes

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