Nitric Acid → HCID 21877762, compound

HRID 1922474Notes

Reaction equation

HRID 1922474 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 93%

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), (5 g, 30.3 mmol) in sulfuric acid, cooled to −5° C. was added nitric acid, fuming (1.413 ml, 30.3 mmol) as a 1:1 mixture in water. The resulting mixture was stirred at −5° C. for 20 min. After 20 min the reaction was quenched via addition of ice, precipitating the product which was collected by filtration. The filter cake was dissolved in dichloromethane and a minimal amount of methanol, dried, filtered and concentrated onto silica gel then chromatographed using 0-10% ethyl acetate in dichloromethane to give the desired 8-fluoro-6-nitro-3,4-dihydroquinolin-2(1H)-one (5.9 g, 28.1 mmol, 93% 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. customAfter 20 min the reaction was quenched via addition of ice
  2. customprecipitating the product which
  3. filtrationwas collected by filtration
  4. dissolutionThe filter cake was dissolved in dichloromethane
  5. dry with materiala minimal amount of methanol, dried
  6. filtrationfiltered
  7. concentrationconcentrated onto silica gel
  8. customthen chromatographed

Sources & evidence

ORD record
ord-86a2d6628f344af8b3694ef31276d8b3
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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