Water → HCID 178483250, compound

HRID 1985874Notes

Reaction equation

HRID 1985874 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:6](=[C:14](OC)[C:15]2[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=2)[C:5]1=[O:24])(=O)C.[CH3:25][N:26]([CH2:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)[CH3:27].[OH-].[Na+].O.[CH3:39][N:40](C)C=O>>[CH3:27][N:26]([CH2:28][C:29]1[CH:35]=[CH:34][C:32]([NH:33]/[C:14](=[C:6]2\[C:5](=[O:24])[NH:4][C:12]3[C:7]\2=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=3)/[C:15]2[CH:16]=[CH:17][C:18]([C:39]#[N:40])=[CH:19][CH:20]=2)=[CH:31][CH:30]=1)[CH3:25]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 308051Benzenemethanamine, 4-amino-N,N-dimethyl-HCID 68676237HCID 68676237, compound2×

Product 1

HCID 178483250HCID 178483250, compound

Conditions

Temperature
80 °C

Procedure

1.07 g of 1-acetyl-3-[1-chloro-1-(4-cyanophenyl)methylene]-6-chloro-2-indolinone (starting material VII) and 0.54 g of 4-(dimethylaminomethyl)aniline (starting material IX.4) are dissolved in 10 ml of dimethylformamide and stirred at 80° C. for 3 hours. After cooling, 1 ml of 6N aqueous sodium hydroxide is added, and the mixture is stirred at room temperature for 30 minutes. Water is added and the mixture is extracted three times with methylene chloride. The combined organic phases are washed twice with water, dried over sodium sulphate and concentrated using a rotary evaporator, and the product is recrystallized from diethyl ether.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred at room temperature for 30 minutes
  3. extractionthe mixture is extracted three times with methylene chloride
  4. washThe combined organic phases are washed twice with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customa rotary evaporator
  8. customthe product is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-09c54c4d7fd64222961121a1417d86ae
Source dataset
uspto-grants-2009_06
Patent number
US07547703B2

Reaction notes

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