Dimethyl Sulfoxide → 1-ethyl-N-(phenylethyl)-1H-pyrazolo[3,4-b]quinoline-4 amine
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
5
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) was heated at 80° C. overnight. The reaction mixture was poured into water (1 L) and the precipitate which formed was collected by filtration and washed with water. The solid was dissolved in hot ethyl acetate, and then the solution was dried over MgSO4, filtered and evaporated to a small volume. Hexane was added and then the mixture was cooled in an ice-bath and then the product which crystallized was 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
- customthe precipitate which formed
- filtrationwas collected by filtration
- washwashed with water
- dissolutionThe solid was dissolved in hot ethyl acetate
- dry with materialthe solution was dried over MgSO4
- filtrationfiltered
- customevaporated to a small volume
- additionHexane was added
- temperaturethe mixture was cooled in an ice-bath
- customthe product which crystallized
- filtrationwas collected by filtration
- washwashed with hexane
- customdried
Sources & evidence
- ORD record
- ord-5cd0eb419d144e02966ab1cd41a346c4
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008226
Reaction notes
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