Reaction equation
Cl[C:2]1[C:3]2[N:4]([N:12]=[CH:13][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][OH:25].C([Li])CCC>C1C=CC=CC=1>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][O:25][C:2]1[C:3]2[N:4]([N:12]=[CH:13][C:14]=2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2.76 g. of 4-chloropyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester in benzene is added dropwise, at 10° to a stirred soluttion of 1.03 g. of 3-dimethylamino-1-propanol and 0.64 g. of butyl lithium in 30 ml. of benzene. The reaction mixture is heated under reflux for 3 hours and is then filtered and concentrated under reduced pressure. The oily residue is dissolved in petroleum ether, treated with carbon and cooled for 12 hours in the refrigerator. The product, 4-[3-(dimethylamino)propoxy]pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester, crystallizes in the form of white needles, m.p. 78°-81°.
Workup
- temperatureThe reaction mixture is heated
- temperatureunder reflux for 3 hours
- filtrationis then filtered
- concentrationconcentrated under reduced pressure
- dissolutionThe oily residue is dissolved in petroleum ether
- additiontreated with carbon
- temperaturecooled for 12 hours in the refrigerator
- customThe product, 4-[3-(dimethylamino)propoxy]pyrazolo[1,5-a]quinoxaline-3-carboxylic acid, ethyl ester, crystallizes in the form of white needles, m.p. 78°-81°
Sources & evidence
- ORD record
- ord-9b5981ab350f4d5ca7503508683b2173
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04128716
Linked notes
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