Sodium Hydroxide → 6-Methyl-5-nitroisoquinoline 2-oxide

HRID 1051246Notes

Reaction equation

HRID 1051246 reaction equation
[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N:7][CH:6]=[CH:5]2.C1C=C(Cl)C=C(C(OO)=[O:23])C=1.[OH-].[Na+]>ClCCl>[CH3:1][C:2]1[C:3]([N+:12]([O-:14])=[O:13])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[N+:7]([O-:23])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 250590506-Methyl-5-nitroisoquinoline

Product 1

HCID 673410166-Methyl-5-nitroisoquinoline 2-oxideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Methyl-5-nitroisoquinoline (43.3 g, 0.230 mol) obtained in Step (2) above was dissolved in dichloromethane (650 mL), and the temperature of the reaction solution was cooled to 0° C. or lower. The reaction solution was slowly added with mCPBA (67.5 g, 0.390 mol), followed by stirring for 10 hours or more at 0° C. The reaction mixture was adjusted to have a pH value of 10 by adding 1N aqueous NaOH solution and extracted with dichloromethane. The combined organic layer thus obtained was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (46.5 g, 99%).

Workup

  1. extractionextracted with dichloromethane
  2. customThe combined organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-619f8c1b3a344f7d872512dcdc0707e9
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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