2-Chloroaniline → 8-Chloro-2,4-dimethylquinoline

HRID 279984Notes

Reaction equation

HRID 279984 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][C:10](=O)[CH:11]=[CH:12][CH3:13].[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[C:12]([CH3:13])[CH:11]=[C:10]2[CH3:9]

Participants

5

Reactant 3

HCID 72402-ChloroanilineHCID 12248PentenoneHCID 14798Sodium Hydroxide

Product 1

HCID 233230688-Chloro-2,4-dimethylquinolineYield 42%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To 4.0 g (0.03 mol) of o-chloroaniline in 50 ml of hydrochloric acid at 100° C. was added dropwise 3.4 g (0.04 mol) of 3-penten-2-one. The mixture was refluxed for 12 hours, then neutralised with 5N sodium hydroxide and extracted with dichloromethane. The organic extract was dried and concentrated to an oil. This was purified on a silica gel column to give 2.54 g (42% of the title product; m.p. 66°-68° C. Anal. Calcd. for C11H10NCl: C, 68.94; H, 5.26; N, 7.31; Cl, 18.50. Found C, 68.87; H, 5.27; N, 7.29; Cl, 18.48.

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. customwas dried
  5. concentrationconcentrated to an oil
  6. customThis was purified on a silica gel column

Sources & evidence

ORD record
ord-d3b86189c004447b8e2d4aa0e3777bc0
Source dataset
uspto-grants-1986_05
Patent number
US04587341

Reaction notes

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