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

HRID 445540Notes

Reaction equation

HRID 445540 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

Conditions

Temperature
120 °C

Procedure

6-Bromo-3-nitro-quinolin-4-ol (Fluorochem Ltd., Derbyshire, UK, 10 g, 37.2 mmol) was added to POCl3 (70 ml). The RM was stirred at 120° C. for 17 h. Then the RM was cooled with an ice-bath, before being slowly dropped onto ice-water. The precipitate was filtered and washed with cold water. The residue was dissolved in DCM, washed with brine, dried over Na2SO4, filtered and evaporated to give the title compound as a beige solid (HPLC tR 3.64 min (Method A))

Workup

  1. temperatureThen the RM was cooled with an ice-bath
  2. additionbefore being slowly dropped onto ice-water
  3. filtrationThe precipitate was filtered
  4. washwashed with cold water
  5. dissolutionThe residue was dissolved in DCM
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-13dbdd9e6c40486cae10f52d006f8cd5
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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