Phosphorus oxychloride → 4-Chloro-6,7-dimethoxy-3-nitroquinoline

HRID 393622Notes

Reaction equation

HRID 393622 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][CH:13]=[C:12]([N+:20]([O-:22])=[O:21])[C:11]2=O>CN(C=O)C>[Cl:3][C:11]1[C:10]2[C:15](=[CH:16][C:17]([O:18][CH3:19])=[C:8]([O:7][CH3:6])[CH:9]=2)[N:14]=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 226465416,7-Dimethoxy-3-nitroquinolin-4(1H)-one

Product 1

HCID 226465674-Chloro-6,7-dimethoxy-3-nitroquinolineYield 83.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (1.69 g, 11 mmol) was added to a suspension of 6,7-dimethoxy-3-nitro-1,4-dihydroquinolin-4-one (2.5 g, 10 mmol) in anhydrous DMF (20 ml) and the mixture was heated at 100° C. for 30 minutes. The mixture was cooled and poured onto ice/water. The precipitate was collected by filtration, washed with water and dried under vacuum to give 4-chloro-6,7-dimethoxy-3-nitroquinoline (2.25 g, 83%).

Workup

  1. temperatureThe mixture was cooled
  2. additionpoured onto ice/water
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7cf39420311e410b8bb610c35329ad3d
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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