Methyl iodide → HCID 22176226, compound

HRID 1797471Notes

Reaction equation

HRID 1797471 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2[OH:19].CI.[C:22](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH3:13])[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2[O:19][CH3:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54725280HCID 54725280, compound

Product 1

HCID 22176226HCID 22176226, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of ethyl 6-chloro-4-hydroxy-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (1.41 g, 5 mmol), methyl iodide (0.47 ml, 7.5 mmol) and potassium carbonate (1.04 g, 7.5 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give ethyl 6-chloro-4-methoxy-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylate (1.11 g, 75.5%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bbe4907e74754072b07c3a6e0a082941
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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