Phosphorus oxychloride → 4-Chloro-6-fluoro-3-nitro-quinoline

HRID 1672313Notes

Reaction equation

HRID 1672313 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-:14])=[O:13])=[C:5]2O.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526770HCID 178526770, compound

Product 1

HCID 108231514-Chloro-6-fluoro-3-nitro-quinoline

Conditions

Temperature
0 °C

Procedure

2.3 g (11 mmol) of 6-fluoro-3-nitro-quinolin-4-ol (Example 19b) in 12 ml POCl3 are heated kept at 130° C. for 4 h. The reaction mixture is cooled to 0° C. and poured into ice-water. A precipitate is formed, which is filtered off and washed with water. The solid material is dissolved in CH2Cl2 and washed with 0.1N NaOH and water. After drying the organic phase over MgSO4, the solvent is evaporated to dryness. The residue is dissolved in a few ml of CH2Cl2 and hexane is added. The title compound precipitates and is filtered off. Drying is done at 60° C. (high-vacuum) overnight. NMR (DMSO-d6): 9.38/s (1H), 8.32/d×d (1H), 8.18/d×d (1H) and 8.02/d×t (1H); HPLC: tret=11.82 min (Grad 1).

Workup

  1. customA precipitate is formed
  2. filtrationwhich is filtered off
  3. washwashed with water
  4. dissolutionThe solid material is dissolved in CH2Cl2
  5. washwashed with 0.1N NaOH and water
  6. dry with materialAfter drying the organic phase over MgSO4
  7. customthe solvent is evaporated to dryness
  8. dissolutionThe residue is dissolved in a few ml of CH2Cl2 and hexane
  9. additionis added
  10. customThe title compound precipitates
  11. filtrationis filtered off
  12. customDrying
  13. customis done at 60° C.
  14. custom(high-vacuum) overnight
  15. customtret=11.82 min (Grad 1)

Sources & evidence

ORD record
ord-198869531d9a497db09e96d5170d79af
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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