m-Chloroperbenzoic acid → 6-Methyl-5-nitroisoquinoline 2-oxide

HRID 1042246Notes

Reaction equation

HRID 1042246 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.ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl>[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-:20])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 250590506-Methyl-5-nitroisoquinoline

Product 1

HCID 673410166-Methyl-5-nitroisoquinoline 2-oxideYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6-Methyl-5-nitroisoquinoline (32 g, 170 mmol) was dissolved in DCM (500 mL) and cooled in an ice-acetone bath to 0° C. 3-Chloroperoxybenzoic acid (49.9 g, 289 mmol) (73%) was added in portions while stirring the reaction mixture vigorously. After the addition, the reaction mixture was stirred at 0° C. for 4 h. Upon being warmed to RT, the reaction mixture was partitioned in DCM/NaOH (aq., 1 N). After multiple extractions, the organic layers were combined and washed with brine then dried over Na2SO4. Removal of the solvent in vacuo gave 6-methyl-5-nitroisoquinoline N-oxide as a yellow solid (23 g). MS (M+H)+205.

Workup

  1. additionAfter the addition
  2. stirringthe reaction mixture was stirred at 0° C. for 4 h
  3. temperatureUpon being warmed to RT
  4. customthe reaction mixture was partitioned in DCM/NaOH (aq., 1 N)
  5. extractionAfter multiple extractions
  6. washwashed with brine
  7. dry with materialthen dried over Na2SO4
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-022bba02a3bb4dbd96f798bc05d44b0a
Source dataset
uspto-grants-2013_10
Patent number
US08557830B2

Reaction notes

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