Acetic Anhydride → 3-Methyl-1,2-dihydroisoquinolin-1-one

HRID 1921326Notes

Reaction equation

HRID 1921326 reaction equation
[CH3:1][C:2]1[N+:3]([O-])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.C(OC(=O)C)(=[O:15])C>>[CH3:1][C:2]1[NH:3][C:4](=[O:15])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 5884573-Methylisoquinoline N-oxide

Product 1

HCID 32444773-Methyl-1,2-dihydroisoquinolin-1-oneYield 27%

Procedure

3-Methyisoquinoline oxide (3.60 g, 22.6 mmol) and acetic anhydride (38 mL) are heated at reflux for 6 hr. After cooling the volatiles are removed and the residue is distilled at 220° C. under 0.5 mbar using a Kugelrohr distillation apparatus to afford 3-methyl-2H-isoquinolin-1-one (900 mg, 27% yield). LC/MS: MS m/e=160 (M+H); RT 2.45 min.

Workup

  1. temperatureat reflux for 6 hr
  2. temperatureAfter cooling the volatiles
  3. customare removed
  4. distillationthe residue is distilled at 220° C. under 0.5 mbar
  5. distillationa Kugelrohr distillation apparatus

Sources & evidence

ORD record
ord-6e77ee63dda04eb78fdf34847c092f2a
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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