N-methyl-2-pyrrolidone → 5-hydroxy-2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-2,3-dihydro-3-pyridazinone

HRID 335442Notes

Reaction equation

[CH3:1][N:2]1[C:7](=[O:8])[C:6]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH3:18])[CH:10]=2)=[C:5](S(C)(=O)=O)[C:4]([CH3:23])=[N:3]1.CN1CCCC1=[O:30].[OH-].[Na+]>O>[OH:30][C:5]1[C:4]([CH3:23])=[N:3][N:2]([CH3:1])[C:7](=[O:8])[C:6]=1[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH3:18])[CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 20 ml volume two-necked flask, 2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-203)-(13)-28) (0.30 g), N-methyl-2-pyrrolidone (1.17 ml), and an aqueous solution of sodium hydroxide (0.14 g) in water (0.6 ml) were added under a nitrogen atmosphere, and stirred at 70° C. for 2 hours. The reaction mixture was added to iced water, and washed with ethyl acetate. The pH of the resulting aqueous layer was adjusted to 5 with cold dilute hydrochloric acid under ice-cooling. The precipitated solids were collected by filtration, washed with water, and dried to give 0.18 g of 5-hydroxy-2,6-dimethyl-4-(1-methyl-1H-indol-3-yl)-2,3-dihydro-3-pyridazinone ((1-201)-(12)-10).

Workup

washwashed with ethyl acetate
temperaturecooling
filtrationThe precipitated solids were collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-e0ff9fcc359f443f857a7a6af9423a0d
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884010B2

Reaction notes

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