Chloroform → (+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900758Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.C(Cl)(Cl)Cl.[C:22](OC(=O)C)(=[O:24])C.C(OC=O)=O>O1CCCC1.CCOCC>[CH:22]([NH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3)=[O:24]

Participants

Conditions

Temperature: 70 °C

Procedure

(+)-2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (1.17 g, 5.08 mmol) was suspended in tetrahydrofuran (30 ml)--chloroform (30 ml). To the suspension, acetic anhydride--formic anhydride (2.24 g, 25.4 mmol) was added, and refluxed with heat in a bath of 70° C. for 3 hours. The resulting reaction mixture was cooled at room temperature, and combined with ether. The insoluble matter, which was collected by filtration, was recrystallized from chloroform--methanol--ether. As a result, 460 mg of the title compound was obtained as colorless powder (35.1%).

Workup

temperaturerefluxed
customThe resulting reaction mixture
temperaturewas cooled at room temperature
filtrationThe insoluble matter, which was collected by filtration
customwas recrystallized from chloroform

Sources & evidence

ORD record: ord-ee8cc227b1ce4f5fb8424173ad72672b
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576324

Reaction notes

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