Potassium Nitrate → 5-Bromo-8-nitroisoquinoline

HRID 880497Notes

Reaction equation

HRID 880497 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2>S(=O)(=O)(O)O>[Br:6][C:7]1[CH:16]=[CH:15][C:14]([N+:1]([O-:4])=[O:2])=[C:13]2[C:8]=1[CH:9]=[CH:10][N:11]=[CH:12]2

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Product 1

HCID 8169835-Bromo-8-nitroisoquinolineYield 82%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Potassium nitrate (1.17 g, 11.59 mmol) was added portion-wise to a solution of 5-bromo-isoquinoline (2.0 g, 9.66 mmol) in concentrated sulphuric acid (10 mL) and stirred at ambient temperature for 1 h. The reaction mixture was quenched with water and basified with aqueous ammonia. The aqueous layer was washed with water, brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford 5-bromo-8-nitro-isoquinoline (2.0 g, 82%) as a yellow solid.

Workup

  1. customThe reaction mixture was quenched with water and basified with aqueous ammonia
  2. washThe aqueous layer was washed with water, brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-05ba0ba67f3c4dd9a85ddd61450113ca
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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