Ammonium Hydroxide → 5-Bromo-8-nitroisoquinoline

HRID 1956477Notes

Reaction equation

HRID 1956477 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.[OH-].[NH4+]>OS(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

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Product 1

HCID 8169835-Bromo-8-nitroisoquinolineYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of potassium nitrate (1.78 g, 8.56 mmol) was added slowly to a solution of 5-bromoisoquinoline in 12 mL H2SO4. After stirring for 3 hours the reaction mixture was poured onto ice and neutralized with conc. ammonium hydroxide. The yellow precipitate was extracted with ethyl acetate (3x), and the combined organic layers were washed with saturated NaCl, dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel (40% ethyl acetate in hexane as eluent) to give 5-bromo-8-nitroisoquinoline in 96% yield.

Workup

  1. extractionThe yellow precipitate was extracted with ethyl acetate (3x)
  2. washthe combined organic layers were washed with saturated NaCl
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (40% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-2ab32a60fb5244a5924a531f3f372cc5
Source dataset
uspto-grants-1998_07
Patent number
US05780493

Reaction notes

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