Methyl iodide → 5-methoxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

HRID 604288Notes

Reaction equation

HRID 604288 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[C:7]2=[O:15].[C:17](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:17][O:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:16])[C:7]2=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 598491785-hydroxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one

Product 1

HCID 598492185-methoxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 5-Hydroxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one (444 mg, 2.0 mmol) and in DMF (5 mL) is added potassium carbonate (553 mg, 4.0 mmol.) and the solution cooled to 0° C. Iodomethane (0.25 mL, 4.0 mmol.) is added and the reaction mixture allow to warm to room temperature and then stirred for 1 hour. The mixture is quenched with a cold water and then the precipitate is filtered, washed with water and dried under vacuum to give a white solid corresponding to 5-methoxy-2-methyl-8-nitro-3,4-dihydro-2H-isoquinolin-1-one (336 mg, 71%).

Workup

  1. temperatureto warm to room temperature
  2. customThe mixture is quenched with a cold water
  3. filtrationthe precipitate is filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-22eb0bb368ea48e69906e6e45e38a0ef
Source dataset
uspto-grants-2011_03
Patent number
US07910585B2

Reaction notes

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