Sodium Hydroxide → 6-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 2245642Notes

Reaction equation

HRID 2245642 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[N-:12]=[N+]=[N-].[Na+].[OH-].[Na+]>ClCCl.CS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:12][CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 1365375-Fluoro-1-indanone

Product 1

HCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-oneYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-Fluoro-indan-1-one (4.00 g, 26.6 mmol) was dissolved in 40 mL dichloromethane and 40 mL methanesulfonic acid. This was cooled to 0° C. and sodium azide (3.46 g, 53.2 mmol) was added. After 2 hours, the solution was made basic by slowly adding 20% aq. sodium hydroxide. The resulting mixture was partitioned between dichloromethane and water. The dichloromethane layer was dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 50 to 100% ethyl acetate/hexanes) to yield 6-Fluoro-3,4-dihydro-2H-isoquinolin-1-one (2.72 g, 16.5 mmol). MS (ESI) 166.1 (M+H)+.

Workup

  1. customThe resulting mixture was partitioned between dichloromethane and water
  2. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (gradient elution 50 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-075691bef40c4c5d8e07bddea76c0d26
Source dataset
uspto-grants-2010_03
Patent number
US07683064B2

Reaction notes

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