Hydrochloric Acid → 3-Chloroisoquinoline

HRID 887185Notes

Reaction equation

HRID 887185 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.Cl.[Sn]>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 313Hydrochloric AcidHCID 2986251,3-DichloroisoquinolineHCID 5352426Tin atom

Product 1

HCID 6409683-Chloroisoquinoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
57.5 °C

Procedure

The product from Example 60B (6.73 g, 33.8 mmol) was suspended in glacial acetic acid (37 mL) and concentrated HCl (13 mL), treated with tin powder (12.1 g, 101.9 mmol), and heated at 55-60° C. for 3 hours with stirring. The mixture was allowed to cool to room temperature and the precipitated tin salts were removed by filtration through Celite. The filtrate was basified to pH 9 with concentrated NH4OH and then extracted with ethyl acetate. The organic extracts were combined, washed with saturated NaHCO3 solution, dried over Na2SO4, and concentrated under reduced pressure to provide the title compound as a gummy yellow residue (1.28 g, 23%).

Workup

  1. temperatureto cool to room temperature
  2. customthe precipitated tin salts were removed by filtration through Celite
  3. extractionextracted with ethyl acetate
  4. washwashed with saturated NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-08c6967250724970843f939be3737cee
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

Loading…