O-Xylene → HCID 14304027, compound

HRID 845296Notes

Reaction equation

HRID 845296 reaction equation
C1(C)C(C)=CC=CC=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=O)[CH:17]([CH3:30])[C:18](=[O:29])[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[Cl:28])=O.[Cl:32][C:33]1[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=1[NH2:35]>C(Cl)(Cl)Cl>[Cl:32][C:33]1[CH:39]=[CH:38][CH:37]=[CH:36][C:34]=1[N:35]1[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[Cl:28])=[CH:19][C:18](=[O:29])[C:17]([CH3:30])=[C:16]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[Cl:9]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 72402-ChloroanilineHCID 19847708HCID 19847708, compound

Product 1

HCID 14304027HCID 14304027, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 200 ml of xylene were added 6.9 g (0.020 mole) of 1,5-bis(2-chlorophenyl)-2-methyl-1,3,5-pentanetrione, 25.5 g (0.20 mole) of 2-chloroaniline and 20.0 g of Molecular Sieves 5A. After heating the reaction mixture under reflux for 2 hours, the reaction mixture was poured into ice water, followed by addition of 200 ml of chloroform thereto and vigorous stirring of the resultant mixture. One hour later, the reaction mixture was filtered to remove solid matter. The organic layer was washed first wtih 50 ml of 10% hydrochloric acid and then with 50 ml of a 10% aqueous solution of sodium hydroxide. The mixture was washed further with water and was then dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (eluent: ethyl acetate) and then recrystallization from acetone to give 1.4 g of 1,2,6-tris(2-chlorophenyl)-3-methyl-4(1H)-pyridinone having a melting point of 205°-207° C.

Workup

  1. temperatureAfter heating the reaction mixture
  2. temperatureunder reflux for 2 hours
  3. filtrationOne hour later, the reaction mixture was filtered
  4. customto remove solid matter
  5. washThe organic layer was washed first wtih 50 ml of 10% hydrochloric acid
  6. washThe mixture was washed further with water
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. customSubsequent to removal of the sodium sulfate
  9. distillationthe solvent was distilled off
  10. customThe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)
  11. customrecrystallization from acetone

Sources & evidence

ORD record
ord-dbf3c3c4eb774a02b4ad239f67062ecb
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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