Phosphorus oxychloride → 4,7-Dichloro-3-nitroquinoline

HRID 1672308Notes

Reaction equation

HRID 1672308 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](O)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:6]1[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526772HCID 178526772, compound

Product 1

HCID 534398754,7-Dichloro-3-nitroquinoline

Procedure

8.5 g 7-chloro-3-nitro-quinolin-4-ol (Example 15a) are heated for 7 h in 80 ml POCl3 under reflux. After standing over night, light yellow needles have formed, which are filtered off and washed with water. The POCl3-filtrate is poured into 1 l of ice-water; additional compound precipitates and is filtered off. The solid materials are dissolved in 300 ml CH2Cl2 and washed first with aqueous sodium hydroxide (300 ml water and 30 ml 2N NaOH), then again with pure water. The organic phase is dried over MgSO4 and evaporated. Colorless needles are formed which are filtered off, washed with hexane, and dried for 16 h at 60° C. (high vacuum). mp: 165-167° C.; MS: 244 (M++1); HPLC: tret=12.88 min (Grad 1).

Workup

  1. temperatureunder reflux
  2. waitAfter standing over night
  3. customlight yellow needles have formed
  4. filtrationwhich are filtered off
  5. washwashed with water
  6. additionThe POCl3-filtrate is poured into 1 l of ice-water
  7. customadditional compound precipitates
  8. filtrationis filtered off
  9. dissolutionThe solid materials are dissolved in 300 ml CH2Cl2
  10. washwashed first with aqueous sodium hydroxide (300 ml water and 30 ml 2N NaOH)
  11. dry with materialThe organic phase is dried over MgSO4
  12. customevaporated
  13. customColorless needles are formed which
  14. filtrationare filtered off
  15. washwashed with hexane
  16. customdried for 16 h at 60° C. (high vacuum)
  17. customtret=12.88 min (Grad 1)

Sources & evidence

ORD record
ord-57925dc03ec34ce79bfcf0c549c21e66
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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