Sodium Methoxide → 1-Methoxy-6-methyl-5-nitroisoquinoline

HRID 840111Notes

Reaction equation

HRID 840111 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:16][O-:17].[Na+]>CO>[CH3:16][O:17][C:2]1[C:11]2[C:6](=[C:7]([N+:13]([O-:15])=[O:14])[C:8]([CH3:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 226222211-Chloro-6-methyl-5-nitroisoquinoline

Product 1

HCID 226222191-Methoxy-6-methyl-5-nitroisoquinolineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred solution of 1-chloro-6-methyl-5-nitroisoquinoline (1.2 g, 5.4 mmol) and sodium methoxide (0.6 g, 95%, 11 mmol) in methanol (20 mL) in a sealed-tube was heated to 80° C. for 2 h, cooled to room temperature and partitioned between ethyl acetate (3×30 mL) and water (50 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate) and concentrated in vacuo to give the product as a beige solid (0.87 g, 74%). A sample recrystallised from ethanol gave mp 94° C.; Found: C, 60.45; H, 4.58; N, 12.74%. C11H10N2O3 requires C, 60.55; H, 4.62; N, 12.83%.

Workup

  1. custompartitioned between ethyl acetate (3×30 mL) and water (50 mL)
  2. washThe combined organic extracts were washed (water, brine)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-997d8b2213a549a383397ef84095e516
Source dataset
uspto-grants-2002_04
Patent number
US06365598B1

Reaction notes

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