Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 23369746 | HCID 23369746 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 23369642 | HCID 23369642 | 111.6% |
Reaction Steps
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%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05576324 |
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| Source dataset | uspto-grants-1996_11 |
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| ORD ID | ord-6c47dd6a858a41578100eac867b1e686 |
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| Source note | uspto-grants-1996_11 |
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