Ammonia → HCID 67087991, compound

HRID 570588Notes

Reaction equation

HRID 570588 reaction equation
[NH3:1].Cl[C:3]1([C:14]2[C:15]([O:20][CH2:21][CH3:22])=[N:16][CH:17]=[CH:18][CH:19]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][C:4]1=[O:13].O>ClCCl>[NH2:1][C:3]1([C:14]2[C:15]([O:20][CH2:21][CH3:22])=[N:16][CH:17]=[CH:18][CH:19]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[NH:5][C:4]1=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 67088050HCID 67088050, compound

Product 1

HCID 67087991HCID 67087991, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

104 ml (728 mmol) of a 7N methanolic ammonia solution were added dropwise to a cooled solution of 47 g (145 mmol) of 3,5-dichloro-3-(2-ethoxypyridin-3-yl)-1,3-dihydroindol-2-one in 250 ml of dichloromethane under a nitrogen atmosphere, and the reaction mixture was then stirred at room temperature overnight. 250 ml of water and 250 ml of dichloromethane were added to the reaction mixture. After stirring for 5 min, a white solid was precipitated and filtered off and washed with water and dichloromethane. Drying in a vacuum drying oven resulted in 26 g of the title compound as a white solid.

Workup

  1. stirringAfter stirring for 5 min
  2. customa white solid was precipitated
  3. filtrationfiltered off
  4. washwashed with water and dichloromethane
  5. customDrying in a vacuum
  6. customdrying oven

Sources & evidence

ORD record
ord-119cee17b8744fe7a24a21245bbda7b7
Source dataset
uspto-grants-2015_05
Patent number
US09023854B2

Reaction notes

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