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

HRID 1930749Notes

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 ice cooling, and the precipitated solids were filtered, so as to obtain the titled compound (21.0 g, 74.5%).

Workup

stirringwhile the reaction solution was stirred under ice cooling
filtrationthe precipitated solids were filtered

Sources & evidence

ORD record: ord-6e21250c1020478ebf703c586b9e0538
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188119B2

Reaction notes

Loading…