Nitric Acid → 6-Fluoro-5-nitroisoquinoline

HRID 1887088Notes

Reaction equation

HRID 1887088 reaction equation
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[F:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[N:16][CH:15]=[CH:14]2>>[F:10][C:11]1[C:12]([N+:1]([O-:4])=[O:2])=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[N:16][CH:15]=[CH:14]2

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 218898476-Fluoroisoquinoline

Product 1

HCID 201540476-Fluoro-5-nitroisoquinoline

Procedure

Under cooling 2.0 mL of concentrated nitric acid are added to 2.8 mL of sulphuric acid. Subsequently 350 mg of 6-fluoroisoquinoline (23) are added, the reaction is warmed up to room temperature and allowed to stir overnight. The reaction mixture is poured on ice, extracted with dichloromethane and adjusted to alkaline pH by addition of sodium hydroxide. The aqueous layer is extracted again with dichloromethane. The dichloromethane layer is dried over magnesium sulfate and evaporated to give 90 mg of 6-Fluoro-5-nitro-isoquinoline, which can be used without further purification. Rt=1.03 min (Method #1). Detected mass: 193.0 (M+H+).

Workup

  1. additionThe reaction mixture is poured on ice
  2. extractionextracted with dichloromethane
  3. additionby addition of sodium hydroxide
  4. extractionThe aqueous layer is extracted again with dichloromethane
  5. dry with materialThe dichloromethane layer is dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-97313429785b48cfa01f1621a39d369f
Source dataset
uspto-grants-2013_08
Patent number
US08501736B2

Reaction notes

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