Carbon Dioxide → HCID 54530367, compound

HRID 1732668Notes

Reaction equation

HRID 1732668 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)=[O:8].N1CCCCC1.C(O)(=O)[CH2:30][C:31]([OH:33])=[O:32].C(=O)=O>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH3:22])=[C:6]([CH:20]=1)[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH:30][C:31]([OH:33])=[O:32])=[CH:14][CH:13]=1)=[O:8]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 8082PiperidineHCID 203044095-Chloro-N-[2-(4-formylphenyl)ethyl]-2-methoxybenzamide

Product 1

HCID 54530367HCID 54530367, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

31.75 g. 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-benzaldehyde (m.p. 115°-116° C.) and 1 ml. piperidine are added to 11.5 g. malonic acid in 100 ml. anhydrous pyridine. The reaction mixture is heated on a waterbath until the evolution of carbon dioxide is finished. After cooling, the reaction mixture is poured on to ice/concentrated hydrochloric acid and the precipitate formed is filtered off with suction, whereafter it is recrystallized from ethanol. There are obained 23.4 g. (about 65% of theory) 4-[2-(5-chloro-2-methoxybenzamido)-ethyl]-cinnamic acid; m.p. 197°-198° C.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is poured on to ice/concentrated hydrochloric acid
  3. customthe precipitate formed
  4. filtrationis filtered off with suction, whereafter it
  5. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-12298c1589584c858408baa211173099
Source dataset
uspto-grants-1980_12
Patent number
US04238506

Reaction notes

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