Sodium Sulfate → 8-Bromo-6-methoxyisoquinoline

HRID 2069081Notes

Reaction equation

HRID 2069081 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[Br:8][C:9]1[CH:10]=[C:11]([O:19][CH3:20])[CH:12]=[C:13]2[C:18]=1[CH2:17][NH:16][CH2:15][CH2:14]2>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[Br:8][C:9]1[CH:10]=[C:11]([O:19][CH3:20])[CH:12]=[C:13]2[C:18]=1[CH:17]=[N:16][CH:15]=[CH:14]2

Participants

5

Reactant 2

HCID 24436Sodium SulfateHCID 674039748-Bromo-6-methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 595347478-Bromo-6-methoxyisoquinolineYield 35.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Sodium sulfate (2.8 g) and manganese dioxide (7.1 g; Ald) were added to a toluene (60 mL) solution of Intermediate 5 (1.99 g) and the resulting mixture was stirred at 140° C. for 24 hours. The reaction mixture was filtrated through celite followed by the addition of 2 N hydrochloric acid and the resulting mixture was washed with ether. The resulting mixture was neutralized with 5 N aqueous sodium hydroxide solution and then extracted with dichloromethane to give the title compound (698 mg).

Workup

  1. filtrationThe reaction mixture was filtrated through celite
  2. additionfollowed by the addition of 2 N hydrochloric acid
  3. washthe resulting mixture was washed with ether
  4. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-3e8e20bb7d444874a7b463aec3541926
Source dataset
uspto-grants-2012_10
Patent number
US08299055B2

Reaction notes

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