Nitric Acid → HCID 21877762, compound

HRID 1922460Notes

Reaction equation

HRID 1922460 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[F:13])=[O:5].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O.O>[F:13][C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 42560293-chloro-N-(2-fluorophenyl)propanamide

Product 1

HCID 21877762HCID 21877762, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-5 °C

Procedure

To a stirred solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (see Example 41 for details) (2 g, 12.11 mmol) in sulfuric acid (12 ml), cooled to −5° C. was added nitric acid, 90% (0.565 ml, 12.11 mmol) as a 1:1 solution in water. The reaction mixture was stirred at −5° C. for 20 min, then quenched via addition of ice, precipitating the product which was collected by filtration. The pale solid was then dissolved in dichloromethane, dried, filtered and concentrated, and then chromatographed on silica gel using 0-10% ethyl acetate in dichloromethane as eluent to give the desired 8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (2.33 g, 11.09 mmol, 92% yield). 1H NMR (DMSO-d6) δ 10.73 (brs, 1H), 8.03 (m, 1H), 8.02 (m, 1H), 3.08 (t, J=7.5 Hz, 2H), 2.57 (t, J=7.5 Hz, 1H).

Workup

  1. customquenched via addition of ice
  2. customprecipitating the product which
  3. filtrationwas collected by filtration
  4. dissolutionThe pale solid was then dissolved in dichloromethane
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel using 0-10% ethyl acetate in dichloromethane as eluent

Sources & evidence

ORD record
ord-ffa6994d787a4ccbbece8dbac04ee105
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

Loading…