Hydrogen Peroxide → 1-benzoyl-1,2-dihydroquinoline-2-carboxamide

HRID 1585568Notes

Reaction equation

HRID 1585568 reaction equation
[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]1[C:19]#[N:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:22].[Na+].OO>CC(C)=O>[C:1]([N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]1[C:19]([NH2:20])=[O:22])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 262191-Benzoyl-1,2-dihydroquinaldonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 2304901-benzoyl-1,2-dihydroquinoline-2-carboxamideYield 55%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-(Benzoyl)-1,2-dihydro-quinoline-2-carbonitrile (26.0 g) was dissolved in acetone (500 mL). Solid sodium bicarbonate (15 g) was added. The mixture was stirred for 30 minutes. 30% Hydrogen peroxide solution (250 mL of a 30% solution) was added drop-wise. After stirring for 4 hours, the acetone was evaporated under vacuum. The residue was acidified with 1N HCl. The precipitate was collected, washed with water and air dried. The solid was slurried in ether then filtered. The title compound (15.3 g) was obtained as an off-white solid, m.p. 169-171° C.

Workup

  1. stirringAfter stirring for 4 hours
  2. customthe acetone was evaporated under vacuum
  3. customThe precipitate was collected
  4. washwashed with water and air
  5. customdried
  6. filtrationthen filtered

Sources & evidence

ORD record
ord-8a21f88e4da84c838575a2c8ae2a96a0
Source dataset
uspto-grants-1999_08
Patent number
US05939435

Reaction notes

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