Methyl Acrylate → HCID 59145902, compound

HRID 887748Notes

Reaction equation

HRID 887748 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:16]([O-:18])=[O:17])=[C:7]([C:12](Br)=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[C:44]([O:48][CH3:49])(=[O:47])[CH:45]=[CH2:46]>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([NH:4][C:5]1[C:6]([N+:16]([O-:18])=[O:17])=[C:7]([C:12](/[CH:46]=[CH:45]/[C:44]([O:48][CH3:49])=[O:47])=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 11151255Methyl 3-acetylamino-6-bromo-2-nitrobenzoate

Product 1

HCID 59145902HCID 59145902, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of methyl 3-(acetylamino)-6-bromo-2-nitrobenzoate (500 mg, 1.58 mmol), palladium acetate (36.0 mg, 0.16 mmol), triphenylphosphine (84.0 mg, 0.32 mmol), potassium carbonate (328 mg, 2.37 mmol) and methyl acrylate (213 μL, 2.37 mmol) in N,N-dimethylformamide (15 mL) was stirred under a nitrogen atmosphere at 110° C. for 30 min with heating. The reaction solution was diluted with water, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→55/45) to give the title compound (303 mg, yield 60%).

Workup

  1. temperaturewith heating
  2. extractionextracted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=25/75→55/45)

Sources & evidence

ORD record
ord-9d8f765538b54503a451a02584afc9e3
Source dataset
uspto-grants-2012_08
Patent number
US08247429B2

Reaction notes

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