Phosphorus oxychloride → HCID 59857990, compound

HRID 1928554Notes

Reaction equation

HRID 1928554 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 recrystallization 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-a20d58d257d14a48a5dd737ccd9d59c8
Source dataset
uspto-grants-2012_05
Patent number
US08183379B2

Reaction notes

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