Pyridine → HCID 67088050, compound

HRID 570587Notes

Reaction equation

HRID 570587 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[C:11]2([C:19]1[C:20]([O:25][CH2:26][CH3:27])=[N:21][CH:22]=[CH:23][CH:24]=1)O.S(Cl)([Cl:30])=O>ClCCl>[Cl:30][C:11]1([C:19]2[C:20]([O:25][CH2:26][CH3:27])=[N:21][CH:22]=[CH:23][CH:24]=2)[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([Cl:7])[CH:9]=2)[NH:13][C:12]1=[O:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 67088040HCID 67088040, compound

Product 1

HCID 67088050HCID 67088050, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4.4 ml (54.3 mmol) of pyridine were added to a suspension of 13.3 g (43.6 mmol) of 5-chloro-3-(2-ethoxypyridin-3-yl)-3-hydroxy-1,3-dihydroindol-2-one from example a.1 in 50 ml of dichloromethane. After the reaction mixture had been cooled to 0° C., 3.8 ml (52.3 mmol) of thionyl chloride was added dropwise. The mixture was stirred at room temperature for one hour and then poured into ice-water. After stirring for 15 minutes, the organic phase was separated off. The aqueous phase was extracted several times with dichloromethane. The combined organic phase was dried over magnesium sulfate and filtered, and the solvent was removed in vacuo. 15.6 g of the title compound were obtained as a yellowish solid which was employed without further purification in the next stage.

Workup

  1. stirringAfter stirring for 15 minutes
  2. customthe organic phase was separated off
  3. extractionThe aqueous phase was extracted several times with dichloromethane
  4. dry with materialThe combined organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5c0043d7c5564d0d97f70d3540d739bf
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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