3',4'-Dimethoxycinnamic acid → HCID 67395909, compound

HRID 470645Notes

Reaction equation

HRID 470645 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:26])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>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:26]=[C:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 168483',4'-Dimethoxycinnamic acidHCID 178443684HCID 178443684, compound2×

Product 1

HCID 67395909HCID 67395909, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

To a solution of 1.35 gm (6.5 mmol) of 3-(3,4-dimethoxy-phenyl)-acrylic acid (compound of Example 2; Step 1) in 6 mL of toluene, 1.14 gm (7.0 mmol) of 1,1-carbonyldiimidazole was added lot wise at 25° C. to 30° C. under inert atmosphere. The mass becomes thick and 5 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-hydroxyoctanimidamide (compound of Example 50; 2.1 g, 13.2 mmol) in 5 mL of toluene was added to the above reaction mixture as one lot at 25° C. to 30° C. The reaction mixture was stirred at 25° C. to 30° C. under nitrogen for 12-14 h, followed by stirring at 100° C. to 105° C. for 6-8 h. After completion of the reaction, the reaction 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 organic layers were combined and washed with 10 mL of 1N HCl solution, 10 mL of 5% sodium bicarbonate solution and 10 mL of 10% sodium chloride solution. The organic layer was distilled to obtain a crude residue, 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
  2. stirringby stirring at 100° C. to 105° C. for 6-8 h
  3. customAfter completion of the reaction
  4. temperaturethe reaction mixture was cooled to 25° C. to 30° C.
  5. customquenched with 10 mL of chilled water
  6. stirringunder stirring at 25° C. to 30° C
  7. customThe organic layer was separated
  8. washthe aqueous layer was washed with 5 mL of toluene
  9. washwashed with 10 mL of 1N HCl solution, 10 mL of 5% sodium bicarbonate solution and 10 mL of 10% sodium chloride solution
  10. distillationThe organic layer was distilled
  11. customto obtain a crude residue, which
  12. customwas purified by column chromatography (silica gel, chloroform-methanol)

Sources & evidence

ORD record
ord-ab3a6997aae349fdb5e8e977691b0298
Source dataset
uspto-grants-2014_01
Patent number
US08629277B2

Reaction notes

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