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

HRID 2415434Notes

Reaction equation

HRID 2415434 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11]2.[N-:18]=[N+]=[N-].[Na+]>C1C=CC=CC=1>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[NH:18][CH2:12][CH2:11]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 787875-Methoxyindan-1-one

Product 1

HCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

Sulfuric acid (82.6 mL) was carefully added, at 0° C., to 5-methoxy-1-indanone (25 g, 154 mmol) in benzene (400 mL) followed by sodium azide (18 g, 277.4 mmol). The resulting mixture was heated at 60° C. for 24 h. After cooling at room temperature, the benzene was evaporated and the resulting mixture was diluted with water and extracted with dichloromethane. After drying of the organic layer with MgSO4, filtration and evaporation the product was obtained as a white solid after purification by chromatography (SiO2, ethyl acetate/n-hexane 1:1 to 4:1 v:v gradient) (13.2 g, 49%). MS: m/e=177.2 (M+)

Workup

  1. temperatureAfter cooling at room temperature
  2. customthe benzene was evaporated
  3. additionthe resulting mixture was diluted with water
  4. extractionextracted with dichloromethane
  5. dry with materialAfter drying of the organic layer with MgSO4, filtration and evaporation the product
  6. customwas obtained as a white solid
  7. customafter purification by chromatography (SiO2, ethyl acetate/n-hexane 1:1 to 4:1 v:v gradient) (13.2 g, 49%)

Sources & evidence

ORD record
ord-c8d47152f0584457a191f6d81627e518
Source dataset
uspto-grants-2004_11
Patent number
US06818774B2

Reaction notes

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