4-Nitrobenzaldehyde → HCID 53983876, compound

HRID 2118950Notes

Reaction equation

HRID 2118950 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][N:14]=1.C(OC(=O)C)(=O)C>O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[CH:12][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 7918Acetic AnhydrideHCID 189224-Methylpyrimidine

Product 1

HCID 53983876HCID 53983876, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

The starting compound is prepared as follows. p-Nitrobenzaldehyde (24.2 g), 4-methyl-pyrimidine (15.5 g) and acetic anhydride (16.7 g) are mixed at room temperature, and the mixture is heated at 120° C. for 5 hours. After cooling, the mixture is poured into water (500 ml), and the aqueous mixture is extracted several times with chloroform. The combined chloroform extracts are dried over magnesium sulfate and concentrated until crystals separated. Addition of ether gives 4-[2-(p-nitrophenyl)ethenyl]pyrimidine (28 g), m.p. 213°-215° C.

Workup

  1. customThe starting compound is prepared
  2. temperatureAfter cooling
  3. extractionthe aqueous mixture is extracted several times with chloroform
  4. dry with materialThe combined chloroform extracts are dried over magnesium sulfate
  5. concentrationconcentrated until crystals
  6. customseparated
  7. additionAddition of ether

Sources & evidence

ORD record
ord-384f58d0299f4858a983b6baee5b5b37
Source dataset
uspto-grants-1987_07
Patent number
US04681884

Reaction notes

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