Acetic Acid → 4-Methoxy-N-(6-dimethylamino-4-benzylamino-3-cyanoquinolin-2-yl)benzamide

HRID 1985682Notes

Reaction equation

HRID 1985682 reaction equation
[CH3:1][O:2][C:3]1[CH:44]=[CH:43][C:6]([C:7]([N:9](C(=O)C2C=CC(OC)=CC=2)[C:10]2[C:19]([C:20]#[N:21])=[C:18]([NH:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:30]([CH3:32])[CH3:31])[CH:16]=3)[N:11]=2)=[O:8])=[CH:5][CH:4]=1.C(O)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C.[OH-].[K+]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:19]([C:20]#[N:21])=[C:18]([NH:22][CH2:23][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N:30]([CH3:31])[CH3:32])[CH:16]=3)[N:11]=2)=[O:8])=[CH:43][CH:44]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 668507214-methoxy-N-(4-methoxybenzoyl)-N-(6-dimethylamino-4-benzylamino-3-cyanoquinolin-2-yl)benzamide

Product 1

HCID 113967974-Methoxy-N-(6-dimethylamino-4-benzylamino-3-cyanoquinolin-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14797Potassium HydroxideSolvent

Procedure

To the solution of 2.3 g of 4-methoxy-N-(4-methoxybenzoyl)-N-(6-dimethylamino-4-benzylamino-3-cyanoquinolin-2-yl)benzamide in 20 mL of acetonitrile, 5 mL of 1N methanolic potassium hydroxide solution is added. The reaction mixture is heated under reflux conditions for 10 minutes, 1.5 mL of glacial acetic acid is added to it, then it is neutralized with 15 mL of 1M sodium hydrogen carbonate solution. The precipitate is filtered off, the yellow crystalline material is recrystallized from the mixture of 5 ml of dimethylformamide and 40 mL of ethanol. After drying 1.3 g of the title compound is obtained, m.p.: 185° C.

Workup

  1. temperatureThe reaction mixture is heated under reflux conditions for 10 minutes
  2. filtrationThe precipitate is filtered off
  3. customthe yellow crystalline material is recrystallized from the mixture of 5 ml of dimethylformamide and 40 mL of ethanol
  4. dry with materialAfter drying 1.3 g of the title compound
  5. customis obtained

Sources & evidence

ORD record
ord-85b74cd2561e4270a49c3fdedc8ad1d5
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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