Phosphorus oxychloride → HCID 59857990, compound

HRID 2378160Notes

Reaction equation

HRID 2378160 reaction equation
[Br: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]>>[Br:1][C:2]1[C:11]([O:12][CH3:13])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([Cl:17])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178486376HCID 178486376, compound

Product 1

HCID 59857990HCID 59857990, compoundYield 84%

Procedure

A mixture of 7-bromo-8-methoxy-2-quinolinol (4c) (2.22 g, 8.7 mmol) and POCl3 (7 mL) was heated under reflux for 1.5 hours. After neutralization with NaHCO3 and extraction with AcOEt, the residue was dissolved in CHCl3 and filtered through silica gel to remove the brown polar impurities. The product (1.99 g, 84% yield) was obtained as white crystals upon recrystalization from AcOEt-Hexanes. mp 130-132° C.; 1H NMR (400 MHz, CDCl3), 8.06 (d, J=8.8 Hz, 1H), 7.66 (d, J=9.2 Hz, 1H), 7.42 (d, J=9.2 Hz, 1H), 7.39 (d, J=8.8 Hz, 1H), 4.17 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. extractionAfter neutralization with NaHCO3 and extraction with AcOEt
  4. dissolutionthe residue was dissolved in CHCl3
  5. filtrationfiltered through silica gel
  6. customto remove the brown polar impurities

Sources & evidence

ORD record
ord-d7834d4530e94686b2db24e03fd3b706
Source dataset
uspto-grants-2008_12
Patent number
US07470788B2

Reaction notes

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