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

HRID 1894675Notes

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>[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 (23.4 g, 110 mmol) described in Manufacturing Example 1-1-2, nitromethane (33.6 g, 550 mmol), ammonium acetate (17.0 g, 220 mmol), and acetic acid (200 mL) was stirred for 1 hour and 45 minutes at 100° C. A small amount of water was added thereto while the reaction solution was stirred under an ice cooling, and the precipitated solids were collected by filtration, so as to obtain title compound (21.0 g, 74.5%).

Workup

stirringwhile the reaction solution was stirred under an ice cooling
filtrationthe precipitated solids were collected by filtration

Sources & evidence

ORD record: ord-5519f5a26a594819a4b9480aeda925ba
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513287B2

Reaction notes

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