Sodium Hydroxide → 3-Chloroisoquinoline

HRID 647424Notes

Reaction equation

HRID 647424 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-Chloroisoquinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 1,3-dichloroisoquinoline (26.0 g; prepared according to the method of G Simchen, Angew. Chem. Internat. Ed. 5 (7), 663, 1966), acetic acid (125 ml), hydrogen iodide (55 ml) and red phosphorus (9.0 g) was heated with stirring at a temperature of 170° C. for a period of 3 hours. After cooling the mixture was poured into ice-water and the aqueous mixture was neutralized with aqueous sodium hydroxide. The aqueous mixture was extracted with dichloromethane and the organic extract was dried over anhydrous magnesium sulfate. The solvent was evaporated to give an oil which was purified by column chromatography over silica gel (eluant dichloromethane) to give 3-chloroisoquinoline (18.23 g) mp<50° C.

Workup

  1. customprepared
  2. temperatureAfter cooling the mixture
  3. extractionThe aqueous mixture was extracted with dichloromethane
  4. extractionthe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customto give an oil which
  8. customwas purified by column chromatography over silica gel (eluant dichloromethane)

Sources & evidence

ORD record
ord-c0053f28893d40fc8672f9d1eee232be
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Reaction notes

Loading…