Water → Ethyl 1,4-dichloro-7-isoquinolinecarboxylate

HRID 2289817Notes

Reaction equation

HRID 2289817 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:10]=2)[C:5](=O)[NH:4][CH:3]=1.O.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=2)[C:2]([Cl:1])=[CH:3][N:4]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 18698325Ethyl 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinecarboxylate

Product 1

HCID 18698389Ethyl 1,4-dichloro-7-isoquinolinecarboxylate

Procedure

Anal. Found: C, 57.02; H, 3.99; N, 5.53. Calc for C12H10ClNO3 : C, 57.27; H, 4.01; N, 5.57. ##STR168## Ethyl 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinecarboxylate (500 mg, 1.99 mmol) was warmed in POCl3 (3 mL) until a clear solution formed, and was then allowed to stand at 23° C. for 18 h. The reaction mixture was poured into warm water, extracted with EtOAc (3×20 mL), and the combined organic extracts washed with water and saturated brine, dried (MgSO4), and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexane-EtOAc (90:10) as eluant followed by crystallisation from i-Pr2O to give ethyl 1,4-dichloro-7-isoquinolinecarboxylate (377 mg, 1.40 mmol) as a pale pink solid.

Workup

  1. customformed
  2. additionThe reaction mixture was poured
  3. extractionextracted with EtOAc (3×20 mL)
  4. washthe combined organic extracts washed with water and saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography upon silica gel
  8. customfollowed by crystallisation from i-Pr2O

Sources & evidence

ORD record
ord-354013117cc141ae86d4269bf9fb3840
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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