m-Chloroperbenzoic acid → 7-methylquinoline-2-carbonitrile N-oxide

HRID 922748Notes

Reaction equation

HRID 922748 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[N:13])=[N:9]2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:22])C=1>ClCCl.C1C=C(Cl)C=C(C(OO)=O)C=1>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]#[N+:13][O-:22])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 107971837-Methylquinoline-2-carbonitrile

Product 1

HCID 895438927-methylquinoline-2-carbonitrile N-oxideYield 94.8%

Reagents, catalysts & solvents 2

HCID 70297m-Chloroperbenzoic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

7-Methylquinoline-2-carbonitrile (181 g, 1.1 mol, 1.0 equiv.) was dissolved in dichloromethane (3.3 L, 0.3 M). m-Chloroperbenzoic acid (500 g, 2.9 mol, 2.6 equiv) was added and the reaction mixture was heated to 40° C. After 3 hr mCPBA (7 g, 40 mmol, 0.04 equiv.) was added and the mixture was allowed to stir overnight at room temperature. The mixture was extracted with 3 L of 1N NaOH aq., washed twice with 20 ml of dichloromethane and the combined organic phases were washed with DI water then dried over MgSO4. The organics were filtered and the solvent was removed to give 192 g of 7-methylquinoline-2-carbonitrile N-oxide (1-4). LRMS m/z (M+H)4 185.2 found, 185.2 required.

Workup

  1. extractionThe mixture was extracted with 3 L of 1N NaOH aq.
  2. washwashed twice with 20 ml of dichloromethane
  3. washthe combined organic phases were washed with DI water
  4. dry with materialthen dried over MgSO4
  5. filtrationThe organics were filtered
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-2d863af8e48541b385eb07bce5f3d201
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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