Nitric Acid → Quinoline, 6-fluoro-8-nitro-

HRID 514824Notes

Reaction equation

HRID 514824 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[N+:12]([O-])([OH:14])=[O:13]>>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 196975Quinoline, 6-fluoro-

Product 1

HCID 154273Quinoline, 6-fluoro-8-nitro-

Procedure

A mixture of 6-fluoroquinoline (2 g, 13.6 mmol) and fuming HNO3 (15 mL) in a round bottom flask equipped with a cooling condenser was refluxed for 100 hours, the resulting mixture was cooled to r.t., poured slowly into crushed ice/H2O, and then the mixture was extracted with DCM (200 mL×3). The combined organic layers were dried over Na2SO4, and concentrated. The residue was passed through a short pad of silica gel to give 1.6 g of title compound. 1H NMR (CHLOROFORM-d) δ: 9.08 (dd, J=4.1, 1.5 Hz, 1H), 8.25 (dd, J=8.5, 1.5 Hz, 1H), 7.89 (dd, J=7.5, 2.8 Hz, 1H), 7.72 (dd, J=8.1, 2.8 Hz, 1H), 7.62 (dd, J=8.4, 4.3 Hz, 1H). LC-MS: m/z 466.6 (M+H)+

Workup

  1. customequipped with a cooling condenser
  2. temperaturewas refluxed for 100 hours
  3. additionpoured slowly
  4. extractionthe mixture was extracted with DCM (200 mL×3)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d1239bb75994ba69eebb365b7eca7f0
Source dataset
uspto-grants-2015_08
Patent number
US09108921B2

Reaction notes

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