Phosphorus oxychloride → 2-Chloro-3-nitroquinoline

HRID 1186455Notes

Reaction equation

HRID 1186455 reaction equation
[N+:1]([C:4]1[C:5](=O)[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 99900612(1H)-Quinolinone, 3-nitro-

Product 1

HCID 126639372-Chloro-3-nitroquinolineYield 95.1%

Conditions

Temperature
110 °C

Procedure

3-Nitroquinolin-2(1H)-one (1.40 g, 7.36 mmol) obtained in Step 1 was dissolved in phosphorus oxychloride (3.50 mL, 36.8 mmol) and the mixture was stirred with heat at 110° C. for 4 hours. The reaction mixture was poured into an ice bath and thereby the reaction was stopped. Then, extraction with ethyl acetate was performed, followed by washing with brine and drying over anhydrous magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 50/1) to give 2-chloro-3-nitroquinoline (1.46 g, yield: 95%).

Workup

  1. additionThe reaction mixture was poured into an ice bath
  2. extractionThen, extraction with ethyl acetate
  3. washby washing with brine
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform/methanol=1/0 to 50/1)

Sources & evidence

ORD record
ord-3fe8f9fc42d04330845db491ba42d9db
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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