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Acetic Acid → 5-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

HRID 2176
Notes
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Reaction equation

HRID 2176 reaction equation
C[O-].[Na+].[C:4]([CH2:6][C:7]([NH2:9])=[O:8])#[N:5].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[CH:20]N(C)C)[CH:18]=O)=[CH:13][CH:12]=1.C(O)(=O)C>CO.O>[C:4]([C:6]1[C:7](=[O:8])[NH:9][CH:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[CH:20]=1)#[N:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 34489722-(4-Chlorophenyl)-3-(dimethylamino)acrylaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 27639105-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Procedure

To solution of sodium methoxide (7.52 g) in methanol (130 ml) was added cyanoacetamide (5.84 g) followed by 2-(4-chlorophenyl)-3-dimethylaminopropenal and the resulting suspension was refluxed overnight. During this time a yellow solid was formed. The mixture was cooled to room temperature and glacial acetic acid (50 ml) was added followed by water (100 ml). The resulting yellow orange solid was filtered off, washed several times with water and dried to yield 8.1 g of 3-cyano-5-(4-chlorophenyl)-2-pyridinone.

Workup

  1. temperaturethe resulting suspension was refluxed overnight
  2. customDuring this time a yellow solid was formed
  3. filtrationThe resulting yellow orange solid was filtered off
  4. washwashed several times with water
  5. customdried

Sources & evidence

ORD record
ord-0e60e058e5c041cbbf3f3bd73811d422
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728715

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes