Nitric Acid → 1-Chloro-5-nitroisoquinoline

HRID 1469703Notes

Reaction equation

HRID 1469703 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[N+:12]([O-])([OH:14])=[O:13].[N+]([O-])([O-])=O.[K+]>OS(O)(=O)=O.O>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 24434Potassium NitrateHCID 140539Isoquinoline, 1-chloro-

Product 1

HCID 4597741-Chloro-5-nitroisoquinoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 1-chloroisoquinoline (3.6 g, 22.09 mmol) in conc. H2SO4 (24 mL) was added conc. HNO3 (8 mL) drop wise at 0-5° C. Then KNO3 (2.90 g, 28.71 mmol) was added to the reaction mixture portion wise at 0-5° C. The reaction mass was stirred at rt for 2 h and diluted with water then the reaction mixture was filtered. The filter cake was dissolved in 5% methanol in chloroform and was dried over Na2SO4. The organic layer was filtered and concentrated to afford 4.0 g of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.74 (t, J=6.9 Hz, 2H), 8.55 (d, J=6.3 Hz, 1H), 8.32 (d, J=6.0 Hz, 1H), 8.02 (t, J=8.1 Hz, 1H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. dissolutionThe filter cake was dissolved in 5% methanol in chloroform
  3. dry with materialwas dried over Na2SO4
  4. filtrationThe organic layer was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5d60ecc2987d4e0cba966db3701d5f20
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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