Phosphorus oxychloride → 4-Chloroquinoline

HRID 1469732Notes

Reaction equation

HRID 1469732 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](O)=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:14]>>[Cl:14][C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516385quinolin-4-ol

Product 1

HCID 691404-Chloroquinoline

Procedure

A solution of 4-quinolinol (1.0 g, 6.88 mmol) in POCl3 (3 mL) was heated at reflux for 2 h. Then the reaction mixture was concentrated and the concentrate was dissolved in EtOAc. The organic layer was washed with a saturated solution of NaHCO3 and water. The organic layer was separated, dried, filtered and concentrated to afford 1.1 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 8.87 (d, J=4.5 Hz, 1H), 8.23 (d, J=7.8 Hz, 1H), 8.14-8.11 (d, J=8.7 Hz, 1H), 7.93-7.88 (t, J=7.5 Hz, 1H), 7.82-7.77 (m, 2H).

Workup

  1. temperatureat reflux for 2 h
  2. concentrationThen the reaction mixture was concentrated
  3. dissolutionthe concentrate was dissolved in EtOAc
  4. washThe organic layer was washed with a saturated solution of NaHCO3 and water
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-42321e85636c457d8cce855c246c3a0c
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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