Phosphorus oxychloride → HCID 21840833, compound

HRID 1739430Notes

Reaction equation

HRID 1739430 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7](=O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([O:21][CH3:22])=[C:10]([O:23][CH3:24])[CH:9]=2)=[O:4].P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:21][CH3:22])=[C:10]([O:23][CH3:24])[CH:9]=2)[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[C:5]([C:3]([O:2][CH3:1])=[O:4])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21840812HCID 21840812, compound

Product 1

HCID 21840833HCID 21840833, compound

Procedure

To phosphorus oxychloride (100 ml) is added 3-methoxycarbonyl-4-(4-pyridyl)-6,7-dimethoxyisoquinolin-1(2H)-one (6 g), and the mixture is heated under reflux for 2.5 hours. The reaction mixture is concentrated, and thereto is added chloroform. To the mixture is further added gradually a saturated aqueous sodium hydrogen carbonate solution, and the mixture is stirred for 20 minutes. The organic layer is collected, dried, and concentrated. The residue is purified by silica gel chromatography (solvent; chloroform:ethyl acetate=5:1) to give 1-chloro-3-methoxycarbonyl-4-(4-pyridyl)-6,7-dimethoxyisoquinoline (5.17 g).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe reaction mixture is concentrated
  4. additionis added chloroform
  5. additionTo the mixture is further added gradually a saturated aqueous sodium hydrogen carbonate solution
  6. customThe organic layer is collected
  7. customdried
  8. concentrationconcentrated
  9. customThe residue is purified by silica gel chromatography (solvent; chloroform:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-5a5e27b7e9de43088d49a9883561dd43
Source dataset
uspto-grants-1999_10
Patent number
US05965730

Reaction notes

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