Dimethyl Sulfoxide → 1-ethyl-N-(phenylethyl)-1H-pyrazolo[3,4-b]quinoline-4 amine

HRID 1458731Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15](Cl)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2].CS(C)=O.[CH2:21]([NH2:29])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([NH:29][CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[C:6]2[CH:5]=[N:4]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-ethyl-4-chloro-1H-pyrazolo[3,4-b]quinoline (11.6 g, 0.05 mol), DMSO (20 ml) and phenethylamine (12.1 g, 0.1 mol) is heated at 80° C. overnight. The reaction mixture is poured into water (1 L), and the precipitate that forms is collected by filtration and washed with water. The solid is dissolved in hot ethyl acetate, and then the solution is dried over MgSO4, filtered and evaporated to a small volume. Hexane is added, and then the mixture is cooled in an ice bath, and then the product that crystallizes is collected by filtration, washed with hexane and dried to afford 12.5 g of 1-ethyl-N-(phenylethyl)-1H-pyrazolo[3,4-b]quinoline-4 amine, m.p. 157°-158° C.

Workup

filtrationthe precipitate that forms is collected by filtration
washwashed with water
dissolutionThe solid is dissolved in hot ethyl acetate
dry with materialthe solution is dried over MgSO4
filtrationfiltered
customevaporated to a small volume
additionHexane is added
temperaturethe mixture is cooled in an ice bath
customthe product that crystallizes
filtrationis collected by filtration
washwashed with hexane
customdried

Sources & evidence

ORD record: ord-c77d079b3d7e40a8b780cce75e3e8d38
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852035

Reaction notes

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