Phosphorus oxychloride → HCID 10537819, compound

HRID 1901469Notes

Reaction equation

HRID 1901469 reaction equation
[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([CH3:15])=[C:8]2[C:3]=1[C:4](=O)[CH2:5][CH:6]=[N:7]2.P(Cl)(Cl)([Cl:19])=O>[OH-].[NH4+]>[Cl:19][C:4]1[C:3]2[C:8](=[C:9]([CH3:15])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:2]=2[CH3:1])[N:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 70275766HCID 70275766, compound

Product 1

HCID 10537819HCID 10537819, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

In a flask is placed 5,8-dimethyl-6-nitro-4-quinolone (3.01 g, 13.8 mmol) with phosphorus oxychloride (41.3 g, 268 mmol). The mixture is refluxed under argon with stirring for 3 hours. After cooling to room temperature the mixture is poured on crushed ice, and concentrated ammonium hydroxide (100mL) is added. Extraction with chloroform (2×200 mL), drying over potassium carbonate, filtration and solvent removal by rotary evaporation gives 4-chloro-5,8-dimethyl-6-nitroquinoline.

Workup

  1. customIn a flask is placed
  2. temperatureThe mixture is refluxed under argon
  3. additionis poured
  4. additionis added
  5. extractionExtraction with chloroform (2×200 mL)
  6. dry with materialdrying over potassium carbonate, filtration and solvent removal by rotary evaporation

Sources & evidence

ORD record
ord-36cff1c26bde483a90caaa2f3f3028bc
Source dataset
uspto-grants-1996_11
Patent number
US05578607

Reaction notes

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