Water → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 1004522Notes

Reaction equation

HRID 1004522 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[N-:13]=[N+]=[N-].[Na+].O.C(=O)([O-])O.[Na+]>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:13][CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 33557Sodium AzideHCID 787875-Methoxyindan-1-oneHCID 516892Sodium Bicarbonate

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-oneYield 43%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-methoxy-1-indanone (1.0 g) in TFA (20 ml) is added sodium azide (4.0 g), and the mixture is refluxed for 1.5 hour. After cooling, the reaction mixture is poured into water (100 ml), and the pH value of the mixture is adjusted to pH 7 with sodium hydrogen carbonate. The mixture is extracted with ethyl acetate, and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and dried over magnesium sulfate. The desiccant is removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (silica gel; 100 g, chloroform/methanol=20:1). The fractions containing the title compound are concentrated under reduced pressure to give the title compound (470 mg) as a pale brown powder.

Workup

  1. temperaturethe mixture is refluxed for 1.5 hour
  2. temperatureAfter cooling
  3. extractionThe mixture is extracted with ethyl acetate
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materiala saturated brine, and dried over magnesium sulfate
  6. customThe desiccant is removed by filtration
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is purified by silica gel column chromatography (silica gel; 100 g, chloroform/methanol=20:1)
  9. additionThe fractions containing the title compound
  10. concentrationare concentrated under reduced pressure

Sources & evidence

ORD record
ord-aef644152b394ac2bae550cfc5ccc8dc
Source dataset
uspto-grants-2000_04
Patent number
US06048854

Reaction notes

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