Diethyl Ether → (+)-2-Formylaminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one
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:18](OC(=O)C)(=[O:20])C.C(OC=O)=O.CCOCC>O1CCCC1.C(Cl)(Cl)Cl>[CH:18]([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:20]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
To a suspension of (-)-aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (965 mg, 4.19 mmol) in a mixture of tetrahydrofuran (30 ml) and chloroform (30 ml), acetic anhydride--formic anhydride (1.83 g, 20.8 mmol) was added and refluxed with heat in a bath of 70° C. for 3 hours. The temperature of the reaction mixture was returned to room temperature. Ether was added to the mixture and insoluble matter was collected by filtration. Recrystallization from chloroform--methanol--ether yielded 410 mg of the title compound as colorless powder (37.9%).
Workup
- temperaturerefluxed
- customwas returned to room temperature
- filtrationwas collected by filtration
- customRecrystallization from chloroform
Sources & evidence
- ORD record
- ord-c799883971d04d7c9aa90577fe37e9e8
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576324
Reaction notes
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