Phosphorus oxychloride → 2-Chloro-6-fluoroquinoline

HRID 1732187Notes

Reaction equation

HRID 1732187 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 98340436-Fluoro-1,2-dihydroquinolin-2-one

Product 1

HCID 150594332-Chloro-6-fluoroquinoline

Procedure

A mixture of the so-prepared 6-fluorocarbostyril (2.9 gm, 0.018 mole) and 30.0 ml of phosphorous oxychloride was refluxed for 1.5 hr. Most of the excess phosphorous oxychloride was then distilled off under aspirator vacuum and the residue poured over crushed ice. The reaction mixture was made nearly neutral with 50% sodium hydroxide. The crude solid product was collected by filtration, taken up in

Workup

  1. temperaturewas refluxed for 1.5 hr
  2. distillationMost of the excess phosphorous oxychloride was then distilled off under aspirator vacuum
  3. additionthe residue poured
  4. customover crushed ice
  5. filtrationThe crude solid product was collected by filtration

Sources & evidence

ORD record
ord-0793f36da021490f8ff5dd1a0618968b
Source dataset
uspto-grants-1980_12
Patent number
US04236912

Reaction notes

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