Methanesulfonic Acid → 6-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 880660Notes

Reaction equation

HRID 880660 reaction equation
[N-:1]=[N+]=[N-].[Na+].[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[CH2:10][CH2:9]2.CS(O)(=O)=O.[OH-].[Na+]>ClCCl>[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:1][CH2:10][CH2:9]2

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 1365375-Fluoro-1-indanone

Product 1

HCID 107257096-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sodium azide (0.870 g, 13.33 mmol) was added in portions to a stirred solution of 5-fluoro-1-indanone (1.0 g, 6.67 mmol) and methanesulfonic acid (4 mL) in dichloromethane (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 18 h. The mixture was then cooled to 0° C. and neutralized with 2N NaOH. The layers were separated, the aqueous layer extracted with dichloromethane, and the combined organic layers were dried over Na2SO4 and concentrated to give the title compound as a white powder. The crude product was used in the next step.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer extracted with dichloromethane
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2235941ad5ed4dad8a3256aef7adacfd
Source dataset
uspto-grants-2015_03
Patent number
US08993593B2

Reaction notes

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