Methyl Acrylate → Methyl 2-acetamido-3-nitrocinnamate

HRID 2306253Notes

Reaction equation

HRID 2306253 reaction equation
[C:1]([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1Br)(=[O:3])[CH3:2].[CH3:15][O:16][C:17](=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([NH:4][C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[CH:19]=[CH:18][C:17]([O:16][CH3:15])=[O:20])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 4643062N-(2-bromo-6-nitrophenyl)acetamide

Product 1

HCID 70171492Methyl 2-acetamido-3-nitrocinnamate

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

N-Acetyl-2-bromo-6-nitroaniline, as described above in Step A, (6.3 g, 24.3 mmol), acrylic acid methyl ester (4.4 mL, 48.64 mmol), triethylamine (4.2 mL, 30.4 mmol) and palladium (11) acetate (275 mg, 1.22 mmol) were dissolved in acetonitrile (75 mL) and heated to 75° C. for 18 hours. The cooled reaction mixture was poured into saturated aqueous Na2CO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from MeOH—H2O to yield the above-titled compound.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from MeOH—H2O

Sources & evidence

ORD record
ord-68e5dac7fd1545ff83136613ce3cb964
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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