Hydrochloric Acid → 1,2,3,4-Tetrahydro-7-nitroisoquinoline

HRID 1640213Notes

Reaction equation

HRID 1640213 reaction equation
S(=O)(=O)(O)O.[CH2:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][NH:7]1.[N+:16]([O-])([O-:18])=[O:17].[K+].Cl>CCO>[N+:16]([C:13]1[CH:14]=[C:15]2[C:10]([CH2:9][CH2:8][NH:7][CH2:6]2)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 24434Potassium Nitrate

Product 1

HCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sulfuric acid (9.90 mL, 0.186 mol) was cooled to 0° C. To the cooled solution was added 1,2,3,4-Tetrahydroisoquinoline (2.5 mL, 020.0 mmol) dropwise via syringe. Potassium nitrate (2.16 g, 0.0214 mol) was then added in small portions over 4 min. The cooling bath was removed and the mixture was allowed to stir at rt for 12 h. Ice was added to the slurry and the mixture basified with NH4OH (precipitate formed). The solution was extracted with chloroform, dried over Na2SO4, filtered, and concentrated to give a brown oil. The oil was dissolved in ethanol (14.8 mL, 0.254 mol) and to this solution was added HCl (2.47 mL, 0.0808 mol). Additional EtOH was added to transfer the precipitated solid for filtration. The white solid was dried under vacuum to yield the desired product without further purification (2.19 g, 51%)

Workup

  1. customThe cooling bath was removed
  2. additionIce was added to the slurry
  3. extractionThe solution was extracted with chloroform
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown oil
  8. filtrationfor filtration
  9. customThe white solid was dried under vacuum

Sources & evidence

ORD record
ord-4499ea8ae6df40a2a6be0ddabd72e285
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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