Phosphorus oxychloride → Methyl 1-chloroisoquinoline-4-carboxylate

HRID 2052802Notes

Reaction equation

HRID 2052802 reaction equation
O=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][NH:3]1.O=P(Cl)(Cl)[Cl:18]>>[Cl:18][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 641184Methyl 1-Oxo-2H-Isoquinoline-4-Carboxylate

Product 1

HCID 3338790Methyl 1-chloroisoquinoline-4-carboxylate

Conditions

Temperature
100 °C

Procedure

A mixture of the product from part 3 (12.5 g) in 50 ml of POCl3 is stirred at 100° C. for about two hours then cooled and concentrated under vacuum. The residue is dissolved in 300 ml of CHCl3, and the resulting solution is washed with aqueous NaHCO3 and water, dried over Na2SO4, filtered and then concentrated to give the title compound, m.p. 53-55° C.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue is dissolved in 300 ml of CHCl3
  4. washthe resulting solution is washed with aqueous NaHCO3 and water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1cea6c6c0ecb4a04851aa14fd91db448
Source dataset
uspto-grants-2008_02
Patent number
US07326709B2

Reaction notes

Loading…