Acetone → 4-(2-Chlorophenyl)-6,8-dimethyl-3-nitroquinoline

HRID 1656430Notes

Reaction equation

HRID 1656430 reaction equation
[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=O.CC(C)=O.Cl.[CH2:24]([N+:28]([O-:30])=[O:29])/[CH:25]=N\O>O>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[C:3]2[C:2](=[C:16]([CH3:17])[CH:15]=[C:14]([CH3:18])[CH:13]=2)[N:1]=[CH:25][C:24]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 149185372-Amino-2'-chloro-3,5-dimethylbenzophenoneHCID 58810166(NZ)-N-(2-nitroethylidene)hydroxylamine

Product 1

HCID 150352094-(2-Chlorophenyl)-6,8-dimethyl-3-nitroquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-2'-chloro-3,5-dimethylbenzophenone (1 g), acetone (50 ml), 20 % hydrochloric acid (20 ml) and methazonic acid (4.5 g, wet) was stirred for 2 hrs. at room temperature and refluxed for 4 hrs. The mixture was diluted with water, and extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by a column chromatography on silica gel to give 4-(2-chlorophenyl)-6,8-dimethyl-3-nitroquinoline as crystals, which was recrystallized from a mixture of methanol and chloroform. m.p. 130°-131° C. Yield 1.95 g (54.2 %).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe residue was purified by a column chromatography on silica gel

Sources & evidence

ORD record
ord-142c9f2e306d4ec3b7503cafb34f7996
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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