Sodium Hydroxide → 3-Chloroisoquinoline

HRID 1913299Notes

Reaction equation

HRID 1913299 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.I.[OH-].[Na+]>C(O)(=O)C>[Cl:12][C:4]1[N:3]=[CH:2][C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24841Hydrogen iodideHCID 2986251,3-Dichloroisoquinoline

Product 1

HCID 6409683-ChloroisoquinolineYield 24.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1,3-dichloroisoquinoline (5.00 g, 25.2 mmol), red phosphorus, (1.72 g, 55.5 mmol), and hydriodic acid (10.5 mL, 58.1 mmol) in acetic acid (25 mL) was heated to reflux for 24 hours. The reaction mixture was cooled and poured onto ice, and the resulting solution brought to pH 7 by the addition of 10N aqueous sodium hydroxide. The solution was extracted with dichloromethane (2×50 mL), and the organic layers concentrated. The residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes) to provide 1.01 g (24%) of the title compound. MS (DCI/NH3) m/z 164 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. additionpoured onto ice
  5. extractionThe solution was extracted with dichloromethane (2×50 mL)
  6. concentrationthe organic layers concentrated
  7. customThe residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-101f5630476747b2a648a093752dd88e
Source dataset
uspto-grants-2013_12
Patent number
US08609692B2

Reaction notes

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