Pyridinium chloride → HCID 135689358, compound

HRID 1655029Notes

Reaction equation

HRID 1655029 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15]C)=[CH:10][CH:9]=2)([O:3][CH3:4])=[O:2].Cl.N1C=CC=CC=1>O>[C:1]([C:5]1[N:6]=[C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([OH:15])=[CH:10][CH:9]=2)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 20077445HCID 20077445, compound

Product 1

HCID 135689358HCID 135689358, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-carbomethoxy-6-methoxy-1-phenylisoquinoline (228 mg) and pyridine hydrochloride (700 mg) was heated at 170° C. for 6 hr. While still hot, H2O (15 mL) was added and the precipitate that formed was collected. The aqueous phase was extracted with EtOAc (5×) and the combined organics were dried (Na2SO4) and concentrated. The residual material was combined with the precipitate and dissolved in MeOH (20 mL) and conc. HCl (10 drops). After refluxing for 60 hr, the mixture was cooled to r.t., NH4OAc buffer was added and the mixture was extracted with EtOAc (3×). The combined organics were washed with buffer, brine, dried (MgSO4) and concentrated. Trituration of the residue with hexane/EtOAc (9:1) provided the title compound as a solid.

Workup

  1. customthe precipitate that formed
  2. customwas collected
  3. extractionThe aqueous phase was extracted with EtOAc (5×)
  4. dry with materialthe combined organics were dried (Na2SO4)
  5. concentrationconcentrated
  6. dissolutiondissolved in MeOH (20 mL)
  7. temperatureAfter refluxing for 60 hr
  8. temperaturethe mixture was cooled to r.t.
  9. additionNH4OAc buffer was added
  10. extractionthe mixture was extracted with EtOAc (3×)
  11. washThe combined organics were washed with buffer, brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-45ea24545566476888708b67dd47303a
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

Loading…