Hydrochloric Acid → HCID 23369642, compound
Reaction equation
[C:1]([CH2:3][CH2:4][CH:5]1[O:19][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.Cl>O1CCCC1>[NH2:2][CH2:1][CH2:3][CH2:4][CH:5]1[O:19][C:8]2=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=[C:7]2[CH2:6]1)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
2-(2-Cyanoethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one (1.35 g) was dissolved in tetrahydrofuran (100 ml), to which lithium aluminum hydride (1.4 g) was added and stirred at 30° C. for 2 hours. To the reaction liquid, methanol (20 ml) was added and stirred for 10 minutes, then filtered through cerite. The filtrate was condensed under reduced pressure, and the resultant crude product was purified by alumina column chromatography (eluent: first, chloroform:ethyl acetate=1:1; later, chloroform:methanol=3:1). Crude crystals (1.05 g) was obtained. These crude crystals were converted into a hydrochloride, which was then recrystallized from a solvent mixture of chloroform-ethanol-ether to obtain 1.53 g of a hydrochloric acid salt of 2-(3-aminopropyl)-5-methyl -2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one as yellow needles (73.4%).
Workup
- additionwas added
- additionwas added
- stirringstirred for 10 minutes
- filtrationfiltered through cerite
- customcondensed under reduced pressure
- customthe resultant crude product was purified by alumina column chromatography (eluent
- customCrude crystals (1.05 g) was obtained
- customwas then recrystallized from a solvent mixture of chloroform-ethanol-ether
Sources & evidence
- ORD record
- ord-6c47dd6a858a41578100eac867b1e686
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576324
Reaction notes
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