Hydrogen Bromide → 1-nitroisoquinoline

HRID 1977672Notes

Reaction equation

HRID 1977672 reaction equation
Br.[N+:2]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][NH:6]1)([O-:4])=[O:3]>CC(O)=O>[N+:2]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][N:6]=1)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 260Hydrogen Bromide2×HCID 18432658HCID 18432658, compound

Product 1

HCID 109867641-nitroisoquinolineYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrobromic acid (3.0 M in HOAc, 1 mL) was added to a suspension of the dihydronitroisoquinoline (0.83 g) in glacial HOAc (2 mL). The mixture was heated to 100° C. for 1 day with occasional addition of more hydrobromic acid solution (3 mL overall). After the reaction, the mixture was allowed to cool to room temperature, concentrated in vacuo, diluted by water, and extracted twice with ethyl ether. Combined organics were washed by saturated NaHCO3 solution, dried over Na2SO4 filtered, concentrated in vacuo, and chromatographed on silica gel (5% to 10% ethyl acetate in hexane) to give 234 mg of nitroisoquinoline (35%) as solids, along with 95 mg of 4-bromo-1(2,4,6-trimethylphenyl)isoquinoline (13%).

Workup

  1. customAfter the reaction
  2. concentrationconcentrated in vacuo
  3. additiondiluted by water
  4. extractionextracted twice with ethyl ether
  5. washCombined organics were washed by saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customchromatographed on silica gel (5% to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-24086d70316e4f628e50d5f1f1b2b444
Source dataset
uspto-grants-2001_05
Patent number
US06235752B1

Reaction notes

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