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

HRID 1971215Notes

Reaction equation

HRID 1971215 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, compound

Product 1

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

Procedure

20 g (74.3 mmol) of 6-bromo-3-nitro-quinolin-4-ol (Example 1b) in 150 ml (1.63 mol) of POCl3 are stirred for 45 min at 120° C. The mixture is cooled to rt and poured slowly into ice-water. The precipitate is filtered off, washed with ice-cold water, and dissolved in CH2Cl2. The organic phase is washed with cold brine, and the aqueous phase is discarded. After drying over MgSO4, the organic solvent is evaporated to dryness to provide the title compound. 1H NMR (CDCl3): δ 9.20/s (1H), 8.54/d (1H), 8.04/d (1H), 7.96/dd (1H); analytical HPLC: tret=4.32 min (Grad 1).

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with ice-cold water
  3. dissolutiondissolved in CH2Cl2
  4. washThe organic phase is washed with cold brine
  5. dry with materialAfter drying over MgSO4
  6. customthe organic solvent is evaporated to dryness

Sources & evidence

ORD record
ord-62e48c694a7e469eb48af93f3e7327e0
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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