Methanesulfonic Acid → 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one

HRID 2069802Notes

Reaction equation

HRID 2069802 reaction equation
CS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2.[N-:17]=[N+]=[N-].[Na+].[OH-].[Na+]>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:17][CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 33557Sodium Azide2×HCID 5206955-Bromo-1-indanone

Product 1

HCID 218654506-Bromo-3,4-dihydro-2H-isoquinolin-1-oneYield 110.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (100 mL) was added to a solution of 5-bromoindanone (25 g, 46 mmol) in CH2Cl2 (200 mL) at 0° C. Sodium azide 10.5 g, 162 mmol) was added slowly in portions to this mixture. After the sodium azide addition was complete, the mixture was stirred for an additional 30 min, and an aqueous mixture of NaOH (20 wt %) was added until the mixture was slightly basic. The mixture was extracted with methylene chloride, and the combined organic layers were evaporated under reduced pressure. Purification of the mixture by flash column chromatography on silica gel (0% to 50% EtOAc/Hexanes then 0% to 7% MeOH/CH2Cl2) provided 11.5 g of 6-Bromo-3,4-dihydro-2H-isoquinolin-1-one. MS (ESI) 226.1 (M+H)+.

Workup

  1. additionwas added until the mixture
  2. extractionThe mixture was extracted with methylene chloride
  3. customthe combined organic layers were evaporated under reduced pressure
  4. customPurification of the mixture by flash column chromatography on silica gel (0% to 50% EtOAc/Hexanes

Sources & evidence

ORD record
ord-46806b7ace3e4cdba18aee8150735303
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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