N-Iodosuccinimide → 4-Iodo-6,7-dimethoxy-1-propylisoquinolin-3-ol

HRID 1620274Notes

Reaction equation

HRID 1620274 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9]([CH2:15][CH2:16][CH3:17])=[N:8][C:7]([OH:18])=[CH:6]2.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[I:31]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CC#N.O>[I:31][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:9]([CH2:15][CH2:16][CH3:17])=[N:8][C:7]=1[OH:18]

Participants

7

Reactant 4

HCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 178440211HCID 178440211, compound2×

Product 1

HCID 1784402504-Iodo-6,7-dimethoxy-1-propylisoquinolin-3-olYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 6,7-dimethoxy-1-propylisoquinolin-3-ol RBO 35142 (2.00 g, 8.09 mmol) and p-toluenesulfonic acid monohydrate (1.50 g, 7.89 mmol) in dry CH3CN (20 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was stirred for 10 min at RT before portionwise addition of N-iodosuccinimide (1.82 g, 8.09 mmol) under vigorous stirring. After 2.5 h, the mixture was slowly poured into a cold solution of NaHCO3 (2.0 g) in 50 mL of water and the solid was filtered, washed with water (50 mL) and dried overnight under vacuum to yield 4-iodo-6,7-dimethoxy-1-propylisoquinolin-3-ol CCH 42098-1 as a brown solid (2.35 g, 78% yield).

Workup

  1. customequipped with a magnetic stirrer
  2. filtrationthe solid was filtered
  3. washwashed with water (50 mL)
  4. customdried overnight under vacuum

Sources & evidence

ORD record
ord-7585eddb38434c84b2ca1e194f9a196e
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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