Hydrochloric Acid → HCID 67087966, compound

HRID 570593Notes

Reaction equation

HRID 570593 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Cl[C:13]1([C:24]2[C:25]([O:30][CH2:31][CH3:32])=[N:26][CH:27]=[CH:28][CH:29]=2)[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=2)[NH:15][C:14]1=[O:23].Cl>CN(C)C=O.ClCCl>[Cl:22][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:23])[C:13]2([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[C:24]1[C:25]([O:30][CH2:31][CH3:32])=[N:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 67088050HCID 67088050, compound

Product 1

HCID 67087966HCID 67087966, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

11.2 ml (98 mmol) of dimethyl malonate were slowly added dropwise to a suspension, cooled to 10° C., of 3.56 g (89 mmol) of sodium hydride (60% dispersion in mineral oil) in 150 ml of dimethylformamide, and the mixture was then stirred at room temperature for 30 minutes. Subsequently, 9.6 g (30 mmol) of 3,5-dichloro-3-(2-ethoxypyridin-3-yl)-1,3-dihydroindol-2-one from example 1.1 were added in portions, and the mixture was stirred at room temperature for 15 min. To work up the reaction it was stirred into cold 1N HCl, and dichloromethane was added. The phases were separated, and the aqueous phase was extracted with dichloromethane. The combined organic phase was washed with water and saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was recrystallized from dichloromethane/pentane. 9.01 g of the title compound were obtained as a yellowish solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 min
  2. customthe reaction it
  3. additionwas added
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with dichloromethane
  6. washThe combined organic phase was washed with water and saturated sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was recrystallized from dichloromethane/pentane

Sources & evidence

ORD record
ord-62c6eaf4150a473dbeeb3d59358b471e
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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