Carbon Dioxide → HCID 53654074, compound

HRID 259596Notes

Reaction equation

HRID 259596 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][CH:6]=1)(=[O:3])[CH3:2].C(=O)=O>[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])[CH3:2])=[CH:19][CH:18]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 2

HCID 280Carbon DioxideHCID 541178672-Acetamido-3-[4-(acetyloxy)phenyl]prop-2-enoic acid

Product 1

HCID 53654074HCID 53654074, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

26.3 g (0.1 mol) of p-acetoxy-α-acetylaminocinnamic acid, 50 ml of quinoline and 2 g of copper powder are heated to 160°-170° C. for 3 hours, in the course of which carbon dioxide is evolved. Thereafter, the quinoline is distilled off in vacuo 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 sodium bicarbonate solution. The organic phase is dried over sodium sulphate and thereafter the solvent is removed by distillation in vacuo. The resulting oil, on crystallisation from ethyl acetate, yields p-(2-acetylaminovinyl)-acetoxybenzene of melting point 165°-166° C.

Workup

  1. distillationThereafter, the quinoline is distilled off in vacuo
  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 sodium bicarbonate solution
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customthe solvent is removed by distillation in vacuo
  7. customThe resulting oil, on crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-e1df4e4869a54de39ede02e7174a0139
Source dataset
uspto-grants-1977_07
Patent number
US04038414

Reaction notes

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