Phosphorus oxychloride → HCID 59857985, compound

HRID 1928550Notes

Reaction equation

HRID 1928550 reaction equation
[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([CH:6]=[CH:7][C:8](O)=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[C:11]([O:12][CH3:13])[C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178493640HCID 178493640, compound

Product 1

HCID 59857985HCID 59857985, compoundYield 90.5%

Procedure

A mixture of 7-fluoro-8-methoxy-2-quinolinol (4a) (2.26 g, 11.7 mmol) and POCl3 (5.5 mL, 60 mmol) was refluxed for 1.5 hours. The contents were concentrated and neutralized with NaHCO3 and the mixture heated with water and AcOEt. The solution was filtered to remove undissolved impurities, followed by extraction. The organic layer was washed with saturated NaCl and dried with MgSO4. The product was recrystallized from ***CHCl3-hexanes, which yielded white crystals (2.24 g, 90% yield): mp 85-86° C.; 1H NMR (400 MHz, CDCl3) 8.06 (d, J=8.8 Hz, 1H) 7.48 (dd, J=8.8, 5.6 Hz, 1H), 7.37 (d, J=8.8 Hz, 1H), 7.35 (dd, J=9.2, 2.4 Hz, 1H), 4.23 (d, J=2.4 Hz, 3H). 19F NMR (376 MHz, CHCl3) −127.35 (dd, J=10.9, 2.6 Hz).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. concentrationThe contents were concentrated
  3. temperaturethe mixture heated with water and AcOEt
  4. filtrationThe solution was filtered
  5. customto remove undissolved impurities
  6. extractionfollowed by extraction
  7. washThe organic layer was washed with saturated NaCl
  8. dry with materialdried with MgSO4
  9. customThe product was recrystallized from ***CHCl3-hexanes, which

Sources & evidence

ORD record
ord-e749eecd2fd64c02ac2beb5d5cf37934
Source dataset
uspto-grants-2012_05
Patent number
US08183379B2

Reaction notes

Loading…