Acetic Anhydride → 6-methoxyisoquinolin-1(2H)-one

HRID 1621296Notes

Reaction equation

HRID 1621296 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N+:8]([O-])[CH:7]=[CH:6]2.C(OC(=O)C)(=[O:16])C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:16])[NH:8][CH:7]=[CH:6]2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 22397333HCID 22397333, compound

Product 1

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

Conditions

Temperature
100 °C

Procedure

5.2 g of 6-Methoxy-isoquinoline 2-oxide (58) was heated in 120 mL of acetic anhydride at 100° C. for 3 h. The reaction mixture was evaporated and the residue was taken up in 2 M NaOH and heated at 100° C. for another hour. The mixture was allowed to cool down and the pH was adjusted by addition of 2N HCl to 6. The aqueous layer was extracted several times with methyl-tert.butyl ether, the combined organic layer was dried over sodium sulphate and evaporated. The crude material was purified by silica gel chromatography to yield 3.26 g of the desired product.

Workup

  1. customThe reaction mixture was evaporated
  2. temperatureto cool down
  3. additionthe pH was adjusted by addition of 2N HCl to 6
  4. extractionThe aqueous layer was extracted several times with methyl-tert.butyl ether
  5. dry with materialthe combined organic layer was dried over sodium sulphate
  6. customevaporated
  7. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-49e9c9a52e5744debcdbb73b7660449b
Source dataset
uspto-grants-2014_07
Patent number
US08772492B2

Reaction notes

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