Carbon Dioxide → HCID 54330864, compound

HRID 1763934Notes

Reaction equation

HRID 1763934 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5](OC)=[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].[NH:23]1[CH2:28][CH2:27]CCC1.[C:29](O)(=O)[CH2:30][C:31]([OH:33])=[O:32].[C:36](=O)=O.ClC1C=CC(OC)=C(C=1)C(NCCC1C=CC(C=CC(O)=O)=CC=1)=O>N1C=CC=CC=1>[CH3:36][C:3]1[CH:2]=[CH:20][CH:27]=[C:28]2[C:4]=1[CH:5]=[C:6]([C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:18][CH:19]=1)=[O:8])[NH:23]2

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 867Malonic AcidHCID 8082PiperidineHCID 203044095-Chloro-N-[2-(4-formylphenyl)ethyl]-2-methoxybenzamideHCID 54530367HCID 54530367, compound

Product 1

HCID 54330864HCID 54330864, 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 obtained 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
  6. customThere are obtained 23.4 g

Sources & evidence

ORD record
ord-453d7a2ec2d94058a44a5ec9071105a9
Source dataset
uspto-grants-1978_09
Patent number
US04113871

Reaction notes

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