Acetic Acid → 3-Methyl-N-(4-benzylamino-3-cyanoquinolin-2-yl)benzamide

HRID 1064354Notes

Reaction equation

HRID 1064354 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[C:5]([N:7](C(=O)C1C=CC=C(C)C=1)[C:8]1[C:17]([C:18]#[N:19])=[C:16]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[OH-].[K+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[C:5]([NH:7][C:8]1[C:17]([C:18]#[N:19])=[C:16]([NH:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 11156487HCID 11156487, compound

Product 1

HCID 99085263-Methyl-N-(4-benzylamino-3-cyanoquinolin-2-yl)benzamideYield 80.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of 5 g of 3-methyl-N-(3-methylbenzoyl)-N-(4-benzylamino-3-cyanoquinolin-2-yl)benzamide in 80 ml of acetonitrile 20 ml of 1N methanolic potassium hydroxide solution are added. The reaction mixture is refluxed for 3 minutes, then 3 ml of glacial acetic acid is added to it, then it is neutralized with 50 ml of 1M sodium hydrogen carbonate solution and the resulting crystals are filtered off. The white crystalline material is recrystallized from 130 ml of acetonitrile to give 3.1 g of the title compound of general formula (I). Mp.: 230° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 minutes
  2. filtrationthe resulting crystals are filtered off
  3. customThe white crystalline material is recrystallized from 130 ml of acetonitrile

Sources & evidence

ORD record
ord-749a0ad361094b509f3cd42dd59d798f
Source dataset
uspto-grants-2005_11
Patent number
US06969723B2

Reaction notes

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