6-methoxyisoquinolin-1(2H)-one → Isoquinoline

HRID 346922Notes

Reaction equation

HRID 346922 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[NH:8][CH:7]=[CH:6]2>O=P(Cl)(Cl)Cl>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:12][CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

3

Reactant 1

HCID 218898546-methoxyisoquinolin-1(2H)-one

Product 1

HCID 8405IsoquinolineYield 120.2%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

6-Methoxy-2H-isoquinolin-1-one (5.0 g, 28.4 mmol) in POCl3 (10 mL) was heated to gentle reflux for 3 h the evaporated in vacuo (Nicolas Briet et al, Tetrahedron, 2002, 5761–5766). The residue was poured into iced water (20 mL) and neutralized to pH 10 with 10 M NaOH. Extracted with CHCl3. The organic layer was washed with brine, dried over MgSO4, filtered, evaporated. The residue was purified by flash chromatography (1:1 hexane-EtOAc) to afford 4.41 g (80%) of the desired product as a white solid.

Workup

  1. temperatureto gentle reflux for 3 h the
  2. customevaporated in vacuo (Nicolas Briet et al, Tetrahedron, 2002, 5761–5766)
  3. additionThe residue was poured into iced water (20 mL)
  4. extractionExtracted with CHCl3
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (1:1 hexane-EtOAc)

Sources & evidence

ORD record
ord-743a9bf13b5d4992ba0ff3300f0be827
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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