3',4'-Dimethoxycinnamic acid → HCID 67396892, compound

HRID 470629Notes

Reaction equation

HRID 470629 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O[NH:17][C:18](=[NH:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]2[O:15][N:28]=[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 168483',4'-Dimethoxycinnamic acidHCID 178443416HCID 178443416, compound2×

Product 1

HCID 67396892HCID 67396892, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of 0.547 g (2.6 mmol) of 3-(3,4-dimethoxy-phenyl)-acrylic acid (compound of Example 2; Step 1) in 8 mL of toluene, 0.46 g (2.8 mmol) of 1,1-carbonyldiimidazole was added in portions at 25° C. to 30° C. under inert atmosphere. To the thick mixture, 1 mL of toluene was added and the resulting mixture was stirred at 25° C. to 30° C. for 60 to 90 min. A solution of N-hydroxy-decanimidamide (compound of Example 32; 1.0 g, 5.3 mmol) in 3 mL of toluene was added to the above reaction mixture at 25° C. to 30° C. The reaction mixture was stirred at 25° C. to 30° C. under nitrogen for 12-14 h and further at 100° C. to 105° C. for 6-8 h. After completion of the reaction, the mixture was cooled to 25° C. to 30° C. and quenched with 10 mL of chilled water under stirring at 25° C. to 30° C. The organic layer was separated, and the aqueous layer was washed with 5 mL of toluene. The combined organic layers was washed with 5 mL of 1N HCl solution, 5 of 5% sodium bicarbonate solution and 5 mL of 10% sodium chloride solution. The organic layer was distilled to yield a crude material, which was purified by column chromatography (silica gel, chloroform-methanol) to yield the title compound.

Workup

  1. stirringThe reaction mixture was stirred at 25° C. to 30° C. under nitrogen for 12-14 h and further at 100° C. to 105° C. for 6-8 h
  2. customAfter completion of the reaction
  3. temperaturethe mixture was cooled to 25° C. to 30° C.
  4. customquenched with 10 mL of chilled water
  5. stirringunder stirring at 25° C. to 30° C
  6. customThe organic layer was separated
  7. washthe aqueous layer was washed with 5 mL of toluene
  8. washThe combined organic layers was washed with 5 mL of 1N HCl solution, 5 of 5% sodium bicarbonate solution and 5 mL of 10% sodium chloride solution
  9. distillationThe organic layer was distilled
  10. customto yield a crude material, which
  11. customwas purified by column chromatography (silica gel, chloroform-methanol)

Sources & evidence

ORD record
ord-ecef4e18f86f4f4d8147bcc6986ddb4c
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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