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

HRID 1073071Notes

Reaction equation

HRID 1073071 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-ccc166e169fa46c2949228b30173b46b
Source dataset
uspto-grants-1990_11
Patent number
US04968676

Reaction notes

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