4-Nitrobenzaldehyde → 2-[(E)-2-(4-Nitrophenyl)ethenyl]pyridine

HRID 330571Notes

Reaction equation

HRID 330571 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:8]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)([O-:10])=[O:9].C(OC(=O)C)(=O)C.C(=O)(O)[O-].[Na+]>>[N+:8]([C:11]1[CH:18]=[CH:17][C:14](/[CH:15]=[CH:1]/[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:13][CH:12]=1)([O-:10])=[O:9]

Participants

5

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 79752-MethylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 53764822-[(E)-2-(4-Nitrophenyl)ethenyl]pyridine

Procedure

A solution of 46.5 g (0.5 mole) of 2-methylpyridine and 75.5 g (0.5 mole) of 4-nitrobenzaldehyde in about 100 g of acetic anhydride (about 1 mole) is refluxed for 6 hours, after which it is carefully poured onto ice water. The stirred mixture is neutralized with saturated, aqueous sodium bicarbonate solution. The precipitate is filtered off under suction, washed with water and recrystallized from ethanol to give 66 g (63% of theory) of reddish brown crystals of melting point 136°-139° C.

Workup

  1. additionafter which it is carefully poured onto ice water
  2. filtrationThe precipitate is filtered off under suction
  3. washwashed with water
  4. customrecrystallized from ethanol
  5. customto give 66 g (63% of theory) of reddish brown crystals of melting point 136°-139° C.

Sources & evidence

ORD record
ord-82de892bb1634cf598b353607d58ea6b
Source dataset
uspto-grants-1990_01
Patent number
US04897425

Reaction notes

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