Sodium Carbonate → 5-Bromo-8-nitroisoquinoline

HRID 272774

Reaction equation

HRID 272774 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[N+:12]([O-])([O-:14])=[O:13].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Product 1

HCID 8169835-Bromo-8-nitroisoquinolineYield 99.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

5-Bromo-isoquinoline (100 mg, 0.48 mmol) was suspended in 0.58 mL of concentrated H2SO4. To this solution was added KNO3 (68 mg, 0.58 mmol) in 0.48 mL of concentrated H2SO4. The reaction mixture was stirred at room temperature for 1.5 hours, poured into water/ice, neutralized with 2.0 M Na2CO3, and extracted with EtOAc three times The combined organic layers were washed brine, dried (MgSO4), filtered and concentrated under vacuum to give 121 mg of the title product. MS (DCI) m/e 255 (M+H)+; 1H NMR (500 MHz, CDCl3) δ 10.0 (s, 1H), 9.39 (s, 1H), 8.85 (d, J=5.76 Hz, 1H), 8.17-8.22 (m, 2H), 8.12 (d, J=8.14 Hz, 1H).

Workup

  1. extractionextracted with EtOAc three times The combined organic layers
  2. washwere washed brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b18b032ac6db43558af4c781acd38ea5
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Linked notes

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