Hydrogen Peroxide → 2-Methyl-4-pyrrolidin-1-yl-quinoline-7-carboxylic acid amide

HRID 1374751Notes

Reaction equation

HRID 1374751 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:17]#[N:18])=[CH:7][CH:8]=2)[N:3]=1.[OH:19]O.[OH-].[Na+]>ClCCl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([C:17]([NH2:18])=[O:19])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 22054486HCID 22054486, compound

Product 1

HCID 694732582-Methyl-4-pyrrolidin-1-yl-quinoline-7-carboxylic acid amideYield 60%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-methyl-4-pyrrolidin-1-yl-quinoline-7-carbonitrile (100 mg, 0.42 mol) in dichloromethane (1 mL) was treated at 0° C. with 30% aq. hydrogen peroxide solution (0.5 mL), tetrabutylammonium hydrogen sulfate (29 mg, 84 μmol), and 20% aq. sodium hydroxide solution (0.5 mL). After removal of the ice bath, the two-phase mixture was stirred at r.t. for 2 h, then the organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 9:1) afforded the title compound (65 mg, 60%). Light brown solid, ISP-MS m/e=256.1 ([M+H]+).

Workup

  1. customAfter removal of the ice bath
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c7d6712f1b614d0484fed3785e668582
Source dataset
uspto-grants-2007_01
Patent number
US07166589B2

Reaction notes

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