Phosphorus oxychloride → 6-Bromo-4-chloro-3-nitroquinoline

HRID 2174938Notes

Reaction equation

HRID 2174938 reaction equation
[Br: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]>>[Br: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]2[Cl:18]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526759HCID 178526759, compound2×

Product 1

HCID 219841286-Bromo-4-chloro-3-nitroquinoline

Procedure

6-Bromo-3-nitroquinolin-4-ol (compound B, 74.3 mmol) and POCl3 (1613 mmol) were stirred for 45 minutes 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 layer was washed with cold brine, and was dried over Na2SO4. The solvent was evaporated to dryness to obtain the title compound. The crude product was used directly for the next step.

Workup

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

Sources & evidence

ORD record
ord-f68b43929a214815b95732b4390c4903
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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