Phosphorus oxychloride → 8-Chloro-2H-[1,3]dioxolo[4,5-g]quinoline

HRID 1825769Notes

Reaction equation

HRID 1825769 reaction equation
[CH2:1]1[O:13][C:12]2[CH:11]=[C:10]3[C:5]([C:6](=O)[CH2:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[O:2]1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:6]1[C:5]2[C:10](=[CH:11][C:12]3[O:13][CH2:1][O:2][C:3]=3[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 66629888HCID 66629888, compound

Product 1

HCID 130857768-Chloro-2H-[1,3]dioxolo[4,5-g]quinoline

Procedure

6,7-Methylenedioxy-4-quinolone (5.0 g, 26.5 mmol) was boiled in POCl3 (75 mL) for 45 min and then cooled. Excess phospohoryl chloride was removed under reduced pressure and ice water (100 mL) was added to hydrolyze any residual phosphoryl chloride. The mixture was basified (pH 9) with ammonium hydroxide, and the solid precipitate was filtered. This material was extracted into ethyl ether (8×100 mL), and the ether solution was dried (MgSO4) and evaporated to provide 4.55 g as a white solid, in 83%; mp 127.5-128° C. (lit. mp 129° C.); 1H NMR (CDCl3) δ 6.15 (s, 2H), 7.35 (d, 1H, J=4.7), 7.39 (s, 1H), 7.49 (s, 1H), 8.56 (d, 1H, J=4.7); 13C NMR (CDCl3) δ 99.8, 102.2, 106.1, 119.9, 123.7, 129.8, 141.2, 147.7, 149.1, 151.4.

Workup

  1. temperaturecooled
  2. customExcess phospohoryl chloride was removed under reduced pressure and ice water (100 mL)
  3. additionwas added
  4. filtrationthe solid precipitate was filtered
  5. extractionThis material was extracted into ethyl ether (8×100 mL)
  6. dry with materialthe ether solution was dried (MgSO4)
  7. customevaporated
  8. customto provide 4.55 g as a white solid

Sources & evidence

ORD record
ord-1bf05f6b66c94e0fb25ace9fa4a37f3c
Source dataset
uspto-grants-2006_05
Patent number
US07049315B2

Reaction notes

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