Ammonium Hydroxide → HCID 18183529, compound

HRID 1358146Notes

Reaction equation

HRID 1358146 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][CH:14]=[C:13]2[C:8]=1[CH:9]=[C:10]([N+:1]([O-:4])=[O:2])[N:11]=[CH:12]2

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 7364875-Bromoisoquinoline

Product 1

HCID 18183529HCID 18183529, compoundYield 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 neutralised 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-3-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-6cb14785236840dd8b8cd14ac10d6e69
Source dataset
uspto-grants-2003_07
Patent number
USRE038200E1

Reaction notes

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