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Hydrochloric Acid → 2-Cyano-3-[4-(dimethylamino)phenyl]prop-2-enoic acid

HRID 1614112
Notes
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Reaction equation

HRID 1614112 reaction equation
[OH-].[Na+].[C:3]([CH2:5][C:6]([O:8]C)=[O:7])#[N:4].[CH3:10][N:11]([CH3:20])[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1.Cl>C(O)C>[C:3]([C:5](=[CH:16][C:15]1[CH:18]=[CH:19][C:12]([N:11]([CH3:20])[CH3:10])=[CH:13][CH:14]=1)[C:6]([OH:8])=[O:7])#[N:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 74794-(Dimethylamino)BenzaldehydeHCID 7747Methyl cyanoacetateHCID 14798Sodium Hydroxide

Product 1

HCID 3679332-Cyano-3-[4-(dimethylamino)phenyl]prop-2-enoic acidYield 37%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Procedure

In 400 ml of an aqueous solution of 13.77 g of sodium hydroxide, 34.80 g of methyl cyanoacetate was dissolved and 34.01 g of p-dimethylamino benzaldehyde was then added under a nitrogen atmosphere, followed by adding 200 ml of ethanol to obtain a uniform solution. Under reflux, the stirring was continued for 51 hours and the reaction mixture was added to 12 N hydrochloric acid to obtain the precipitates. The resultant solid was repeated twice to recrystallize from a methanol/ethanol mixture to obtain 13.51 g of the needles.

Workup

  1. customto obtain a uniform solution
  2. temperatureUnder reflux
  3. customto obtain the precipitates
  4. customto recrystallize from a methanol/ethanol mixture

Sources & evidence

ORD record
ord-875369f899494c43bb2105bfeaca2bd0
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05196147

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes