Phosphorus oxychloride → 6-Bromo-2-chloro-4-methylquinoline

HRID 2112818Notes

Reaction equation

HRID 2112818 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=O)[CH:11]=[C:10]2[CH3:18]>N>[Br:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([Cl:3])[CH:11]=[C:10]2[CH3:18]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 63244626-Bromo-4-methylquinolin-2-ol

Product 1

HCID 47381436-Bromo-2-chloro-4-methylquinoline

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

25 mL of phosphorus oxychloride is added to 2.7 g (11.34 mmol) of 6-bromo-4-methyl-1H-quinolin-2-one (Example 1b) and the reaction mixture is refluxed for 2 hours. After cooling, the mixture is added batchwise to 250 mL of 10% NH3 solution, the precipitate formed is filtered off, washed with water, and dried in the circulating air dryer at 30° C. Yield: 2.7 g (93% of theoretical); C10H7BrClN (M=256.526); calc.: molpeak (M+H)+: 256/258/260 (BrCl); found: molpeak (M+H)+: 256/258/260 (BrCl); Rf value: 0.95 (silica gel, DCM/MeOH 9:1).

Workup

  1. temperaturethe reaction mixture is refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. washwashed with water
  6. customdried in the circulating air dryer at 30° C

Sources & evidence

ORD record
ord-6592801dfbd7497abd907d44c6626dae
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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