Hydrogen Bromide → 1-nitroisoquinoline

HRID 2305314Notes

Reaction equation

HRID 2305314 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-48aec90faf5a496db1896eb14df6e456
Source dataset
uspto-grants-2002_08
Patent number
US06440969B2

Reaction notes

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