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

HRID 655699
Notes
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Reaction equation

HRID 655699 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342Acetonitrile
Solvent
HCID 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-e94fa77d1e7e49cf897b6b87034d9db7
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08071601B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes