Acetone → HCID 53741968, compound

HRID 1900777Notes

Reaction equation

HRID 1900777 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH3:12])([O-])=O.[H][H].CC(C)=O.[C:19](Cl)(=[O:28])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(C)C.CO.C(Cl)(Cl)Cl.[Pd].N1C=CC=CC=1>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:4]([NH:1][C:19](=[O:28])[CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:5]([CH3:12])[CH:6]=1

Participants

9

Reactant 4

HCID 180AcetoneHCID 660233-Phenylprop-2-enoyl chlorideHCID 793303-Methyl-4-nitroanisoleHCID 178418361HCID 178418361, compound

Product 1

HCID 53741968HCID 53741968, compoundYield 95.5%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 21255859Isopropanol methanolSolvent

Conditions

Temperature
0 °C

Procedure

2-Nitro-5-methoxytoluene (24.9 g, 149 mmol) was dissolved in a solvent mixture (150 ml) of isopropanol--methanol (2:1). To the solution, 10% palladium-on-carbon (500 mg) was added, followed by stirring at room temperature for 5 hours in the atmosphere of hydrogen. After the reaction, the catalyst was removed by filtration, and the filtrate was condensed. The resultant residue was combined with acetone (150 ml) and pyridine (14.2 ml), and the mixture was cooled to 0° C. and stirred. Cinnamoyl chloride (18.5 g, 111 mmol) was added thereto and the mixture was stirred overnight at room temperature. The reaction mixture was condensed, and the residue was dissolved in chloroform, followed by washing with water, 2N-HCl, and aqueous NaCl solution in this order. The washed material was dried and condensed to obtain 28.33 g of N-(4-methoxy-2methylphenyl)cinnamamide as colorless needles (71.2%).

Workup

  1. customAfter the reaction
  2. customthe catalyst was removed by filtration
  3. customcondensed
  4. stirringthe mixture was stirred overnight at room temperature
  5. customcondensed
  6. washby washing with water, 2N-HCl, and aqueous NaCl solution in this order
  7. customThe washed material was dried
  8. customcondensed

Sources & evidence

ORD record
ord-2c2975aa533744b28a1fa83c10068758
Source dataset
uspto-grants-1996_11
Patent number
US05576324

Reaction notes

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