Hydrogen Peroxide → 4-(6-Methoxyquinolin-2-yl)benzamide

HRID 1472665Notes

Reaction equation

HRID 1472665 reaction equation
N1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([C:12]3[C:21](C)=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:23][CH3:24])[CH:18]=4)[N:13]=3)=[CH:8][CH:7]=2)=[N:4]N=N1.[OH-:25].[Na+].OO>CS(C)=O>[CH3:24][O:23][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([C:9]1[CH:10]=[CH:11][C:6]([C:5]([NH2:4])=[O:25])=[CH:7][CH:8]=1)[CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 178487824HCID 178487824, compound2×

Product 1

HCID 669800514-(6-Methoxyquinolin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-(6-methoxyquinolin-2-yl)benzonitrile (5.00 g, 15.4 mmol, prepared following Scheme 2, Step 1 starting from Intermediate 1 and 4-cyanophenylboronic acid) in DMSO (40 mL) was added aqueous NaOH (1M, 10 mL). The mixture was cooled to 0° C. The aqueous H2O2 (30%, 30 mL) was added dropwise. After addition, the mixture was stirred at 0° C. for 30 minutes. The mixture was quenched with saturated Na2SO3 (100 mL) and filtered. The precipitate was washed with H2O (50 mL) and MeOH (50 mL). The filter cake was dried via high vacuum to give the desired product (5.50 g, yield: 99+%) as a solid.

Workup

  1. additionAfter addition
  2. customThe mixture was quenched with saturated Na2SO3 (100 mL)
  3. filtrationfiltered
  4. washThe precipitate was washed with H2O (50 mL) and MeOH (50 mL)
  5. customThe filter cake was dried via high vacuum

Sources & evidence

ORD record
ord-74495945b7d1424c9b0370941832eefe
Source dataset
uspto-grants-2015_04
Patent number
US09012646B2

Reaction notes

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