p-Nitroacetophenone → (2E)-1-(4-nitrophenyl)-3-pyridin-4-ylprop-2-en-1-one

HRID 227604

Reaction equation

HRID 227604 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:13]1[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][CH:14]=1.[OH-].[Na+]>O.O.C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:12])/[CH:11]=[CH:19]/[C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7487p-NitroacetophenoneHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 6088197(2E)-1-(4-nitrophenyl)-3-pyridin-4-ylprop-2-en-1-oneYield 25.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A suspension of 4′-nitroacetophenone (5 g, 30.3 mmol) and 4-pyridinecarboxaldehyde (2.89 mL, 30.3 mmol) in water (45 mL) at room temperature was treated with 6% NaOH in H2O/ethanol (2:1)(0.606 mL), stirred overnight, and filtered. The filter cake was washed with water and small amount of ethanol then triturated with dichloromethane to provide 1.95 g (25%) of the desired product. MS(ESI(+)) m/e 255 (M+H)+.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with water and small amount of ethanol
  3. customthen triturated with dichloromethane

Sources & evidence

ORD record
ord-66be6540069849619d3c20efa2b68ca7
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Linked notes

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