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

HRID 557261Notes

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 described in Preparation Example 1-3-2 (23.4 g, 110 mmol), nitro methane (33.6 g, 550 mmol), ammonium acetate (17.0 g, 220 mmol) and acetic acid (200 mL) was stirred at 100° C for one hour 45 minutes. While the reaction solution was being stirred under ice cooling, small amount of water was added thereto, and the precipitated solids were filtered to obtain title compound (21.0 g).

Workup

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

Sources & evidence

ORD record: ord-9f0d9889a1b54017bb63e14bfec34e84
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058444B2

Reaction notes

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