Ethyl Acrylate → HCID 66960160, compound

HRID 2247474Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C=O)C>[CH2:18]([O:17][C:13](=[O:16])/[CH:14]=[CH:15]/[C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1)[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

To a DMF (20 mL) solution of 5-bromo-3-methoxy-2-nitropyridine (726 mg) synthesized according to the method described in Acta Chemica Scandinavica vol. 47, p. 805, 1993, ethyl acrylate (0.44 mL), palladium acetate (35 mg), 2-(di-tert-butylphosphino) biphenyl (93 mg) and TEA (0.87 mL) were added, and the reaction solution was agitated at 80° C. for 3 hours. After the reaction solution was allowed to be cooled to room temperature, ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution to separate an organic layer. After the obtained organic layer was dried over anhydrous magnesium sulfate, solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1), and 787 mg (69%) of (E)-3-(5-methoxy-6-nitropyridin-3-yl)acrylic acid ethyl ester was obtained. The physical properties of the compound are as follows.

Workup

temperatureto be cooled to room temperature
customto separate an organic layer
dry with materialAfter the obtained organic layer was dried over anhydrous magnesium sulfate, solvent
customwas evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1)

Sources & evidence

ORD record: ord-582af2d39f5a462cbe4c887d97658d2e
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687640B2

Reaction notes

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