Carbon Dioxide → HCID 68117788, compound

HRID 259618Notes

Reaction equation

HRID 259618 reaction equation
[C:1]([O:4][C:5]1[CH:19]=[CH:18][C:8]([CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])C(O)=O)=[CH:7][C:6]=1OC)(=[O:3])[CH3:2].[C:22](=O)=[O:23]>[Cu].N1C2C(=CC=CC=2)C=CC=1>[C:15]([NH:14][CH:10]=[CH:9][C:8]1[CH:7]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH2:2][O:23][CH3:22])=[CH:19][CH:18]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 280Carbon DioxideHCID 27543002-(Acetylamino)-3-[4-(acetyloxy)-3-methoxyphenyl]-2-propenoic acid

Product 1

HCID 68117788HCID 68117788, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

18.0 g (0.06 mol) of 4-acetoxy-α-acetylamino-3-methoxycinnamic acid are heated with 30 ml of quinoline and 1.2 g of copper powder to 160°-170° C. for 3 hours, in the course of which carbon dioxide is evolved. Thereafter, the quinoline is distilled off under reduced pressure and the residual mass is taken up in ethyl acetate. After filtering off the copper powder, the ethyl acetate solution is extracted with 25 ml of 1 N hydrochloric acid and is then washed with water and subsequently with sodium bicarbonate solution. The organic phase is dried over sodium sulphate and thereafter the solvent is removed by distillation under reduced pressure. The resulting oil yields 4-(2-acetylaminovinyl)-2-methoxy-acetoxybenzene, of melting point 169°-170° C., from ethyl acetate.

Workup

  1. distillationThereafter, the quinoline is distilled off under reduced pressure
  2. filtrationAfter filtering off the copper powder
  3. extractionthe ethyl acetate solution is extracted with 25 ml of 1 N hydrochloric acid
  4. washis then washed with water and subsequently with sodium bicarbonate solution
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customthe solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4a42659e90bd4d959a5c3ce0912c6528
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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