Nitric Acid → HCID 21877762, compound

HRID 723911Notes

Reaction equation

HRID 723911 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[F:1][C:2]1[CH:3]=[C:4]([N+:13]([O-:15])=[O:14])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 151448738-Fluoro-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 21877762HCID 21877762, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-5 °C

Procedure

8-Fluoro-3,4-dihydro-1H-quinolin-2-one [prepared according to the procedure found in EP0524846] (2.62 g, 0.0159 mol) is dissolved in concentrated sulfuric acid (20 ml) and cooled to −5° C. Nitric acid (70%, 1.02 ml, 0.0159 mol) is added dropwise and the reaction stirred at −5° C. for 20 minutes. The mixture is poured onto ice and the resulting precipitate collected by filtration, washed well with water, and dried under vacuum. Purification by flash column chromatography (30% ethyl acetate/hexane) gives the title compound as a light yellow solid (2.50 g, 75%); [M+H]+=211.

Workup

  1. additionThe mixture is poured onto ice
  2. filtrationthe resulting precipitate collected by filtration
  3. washwashed well with water
  4. customdried under vacuum
  5. customPurification by flash column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f9ecd6c29b8d46df9d067d2acfbefb4d
Source dataset
uspto-grants-2006_11
Patent number
US07141588B2

Reaction notes

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