Acetic Acid → 4-Methyl-2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

HRID 1691005Notes

Reaction equation

C(O)(=O)C.[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[CH:7]=1.[N+:22]([CH3:25])([O-:24])=[O:23].C([O-])(=O)C.[NH4+]>C(OCC)(=O)C.O>[CH3:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([O:12][CH2:13][C:14]2[CH:21]=[CH:20][C:17](/[CH:18]=[CH:25]/[N+:22]([O-:24])=[O:23])=[CH:16][CH:15]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To an acetic acid (20.0 mL) solution of 4-(4-methyl-pyridin-2-yloxymethyl)-benzaldehyde (2.60 g, 11.5 mmol) described in Manufacturing Example 43-1-2 were added nitromethane (3.50 g, 57.3 mmol) and ammonium acetate (1.76 g, 22.9 mmol) at room temperature under nitrogen atmosphere, which was stirred for 4 hours at 100° C. Water and ethyl acetate were added to the reaction mixture, and the organic layer was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.40 g) as a crude product.

Workup

extractionthe organic layer was extracted with ethyl acetate
customThe organic layer was separated
washwashed with water and saturated aqueous sodium chloride
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record: ord-252fefde3e8b4604871f8cc15ff5abe1
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153662B2

Reaction notes

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