Phosphorus oxychloride → Methyl 1-chloroisoquinoline-4-carboxylate

HRID 1826826Notes

Reaction equation

HRID 1826826 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-1d307f716c314e11a2b42032ec49d8b2
Source dataset
uspto-grants-2006_05
Patent number
US07053093B2

Reaction notes

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