P-Anisidine → HCID 532094, compound

HRID 1014377Notes

Reaction equation

HRID 1014377 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:16][C:17]([CH3:22])=[CH:18][C:19](Cl)=[O:20]>CC(C)=O.O>[CH3:16][C:17]([CH3:22])=[CH:18][C:19]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:20]

Participants

6

Reactant 3

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 1023943-Methyl-2-butenoyl chloride

Product 1

HCID 532094HCID 532094, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of p-anisidine (10 g, 81 mmol, Aldrich) and potassium carbonate (13.5 g, 97.5 mmol, Aldrich) in acetone (125 mL) was cooled to 0° C. and treated with dimethyl acryloyl chloride (10.2 mL, 89.3 mmol). The mixture was allowed to warm to room temperature overnight. The reaction was diluted with water and extracted with dichloromethane. The organic layer was separated, dried over magnesium sulfate, filtered, concentrated, and purified by chromatography on SiO2 (0 to 100% ethyl acetate/dichloromethane) to give 3-methyl-N[4-(methyloxy)phenyl]-2-butenamide (12.4 g, 67%) as a light violet solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.84 (s, 3 H), 2.13 (s, 3 H), 3.71 (s, 3 H), 5.82 (s, 1 H), 6.85 (d, J=9.0 Hz, 2 H), 7.52 (d, J=9.0 Hz, 2 H), 9.67 (s, 1 H); ESIMS (M+H)+=206.

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionextracted with dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by chromatography on SiO2 (0 to 100% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-3d95edef5e1f4fff8169d23a6a190bac
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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