Hydrochloric Acid → 2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-5-methylsulfonyl-2,3-dihydro-3-pyridazinone

HRID 579255Notes

Reaction equation

HRID 579255 reaction equation
[CH3:1][N:2]([C:11](=[O:24])[C:12]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH3:23])[CH:15]=1)=O)[N:3]=[C:4]([CH3:10])[CH2:5][S:6]([CH3:9])(=[O:8])=[O:7].CO.O.[OH-].[Li+].Cl>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:11](=[O:24])[C:12]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([CH3:23])[CH:15]=2)=[C:5]([S:6]([CH3:9])(=[O:8])=[O:7])[C:4]([CH3:10])=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 866893561-methyl-1-[2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazine

Product 1

HCID 666955622,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-5-methylsulfonyl-2,3-dihydro-3-pyridazinoneYield 89.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a 50 ml volume three-necked flask, 1-methyl-1-[2-(1-methyl-1H-indol-3-yl)-2-oxoacetyl]-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-203)-(13)-28) (2.0 g), methanol (7.59 ml), and toluene (2.31 ml) were added under a nitrogen atmosphere, then added lithium hydroxide monohydrate (0.24 g) under cooling on ice-bath of −5° C., and stirred for 2 hours. To the mixture, cold dilute hydrochloric acid was added under ice-cooling, and stirred for 5 minutes. Then, the mixture was added to ice water. The precipitated solids were collected by filtration, and dried under reduced pressure to give 1.7 g of 2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-203)-(13)-28).

Workup

  1. temperaturecooling
  2. stirringstirred for 5 minutes
  3. filtrationThe precipitated solids were collected by filtration
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-352edc7530c34ba3a7ea78ef02935f71
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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