Phosphorus oxychloride → Quinoline, 4,6-dichloro-3-nitro-

HRID 476153Notes

Reaction equation

HRID 476153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2O.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[N:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526764HCID 178526764, compound2×

Product 1

HCID 10681670Quinoline, 4,6-dichloro-3-nitro-

Procedure

6-Chloro-3-nitroquinolin-4-ol (Compound of step 2, 5 g, 22.42 mmol) in POCl3 (150 mL, 493 mmol) was stirred for 45 min at 120° C. The mixture was cooled to RT and poured slowly into ice-water. The precipitate was filtered, washed with ice-cold water, and dissolved in CH2Cl2. The organic phase was washed with cold brine and dried over Na2SO4. The organic solvent was evaporated to dryness to obtain the title compound.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ice-cold water
  3. dissolutiondissolved in CH2Cl2
  4. washThe organic phase was washed with cold brine
  5. dry with materialdried over Na2SO4
  6. customThe organic solvent was evaporated to dryness

Sources & evidence

ORD record
ord-8e3351cd1f964ade91403170bb04b6e9
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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