Phosphorus oxychloride → 2-Chloro-8-methylquinoline

HRID 1626425

Reaction equation

HRID 1626425 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N+:10]([O-])=[CH:9][CH:8]=[CH:7]2.P(Cl)(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:15][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 12488418Quinoline, 8-methyl-, 1-oxide

Product 1

HCID 215401952-Chloro-8-methylquinolineYield 81.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-methylquinoline 1-oxide (0.440 g, 2.764 mmol) in toluene (10 ml) was added phosphoryl trichloride (1.265 ml, 13.82 mmol), and the reaction was heated to 80° C. for 2 hours. The reaction was cooled to ambient temperature and concentrated. The crude material was taken up in EtOAc and washed with saturated sodium bicarbonate and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to yield the desired compound (0.4 g, 2.252 mmol, 81.47% yield).

Workup

  1. temperatureThe reaction was cooled to ambient temperature
  2. concentrationconcentrated
  3. washwashed with saturated sodium bicarbonate and saturated sodium chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d263980c4bda4320b5b4930f4bff2cf5
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Linked notes

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