Carbon Dioxide → Ethyl 3-(4-aminophenyl)acrylate

HRID 1758216Notes

Reaction equation

HRID 1758216 reaction equation
C1COCC1.[CH2:6]([O:8][C:9](=[O:21])[CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[CH3:7].O.C(=O)=O>C(O)C>[CH2:6]([O:8][C:9](=[O:21])[CH:10]=[CH:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)[CH3:7]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 8028TetrahydrofuranHCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoate

Product 1

HCID 97826Ethyl 3-(4-aminophenyl)acrylateYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen, 17.5 g (19.4 mmol) lithium-cobalt (I) phthalocyanine×4.5 THF and 663 mg (3 mmol) p-nitro cinnamic ethyl ester are agitated in 100 ml ethanol for 65 hours at 20° C. The green reaction mixture is mixed with 10 ml water; CO2 and air are passed into it for 5 min. and the blue precipitate is centrifuged which is washed out with ethanol and ether. The centrifugate collected is concentrated and the residue separated into methylene chloride and water. Concentration of the organic phase, dried with sodium sulfate, produces 470 mg (82%) p-amino cinnamic ethyl ester.

Workup

  1. washis washed out with ethanol and ether
  2. customThe centrifugate collected
  3. concentrationis concentrated
  4. customthe residue separated into methylene chloride and water
  5. dry with materialConcentration of the organic phase, dried with sodium sulfate

Sources & evidence

ORD record
ord-2898c3846b6542baa990df84ca17d553
Source dataset
uspto-grants-1983_02
Patent number
US04372893

Reaction notes

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