Cyclopropylamine → 1-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 1073607Notes

Reaction equation

[CH:1]1([NH2:4])[CH2:3][CH2:2]1.Cl[C:6]1[C:15]([C:16]([C:18](=[CH:24]N(C)C)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:17])=[CH:14][C:13]2[C:8](=[C:9]([F:30])[C:10]([F:29])=[C:11]([F:28])[CH:12]=2)[N:7]=1>ClC(Cl)Cl.C(O)C.C1CCN2C(=NCCC2)CC1>[CH:1]1([N:4]2[C:6]3[N:7]=[C:8]4[C:9]([F:30])=[C:10]([F:29])[C:11]([F:28])=[CH:12][C:13]4=[CH:14][C:15]=3[C:16](=[O:17])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:24]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

4.12 g of cyclopropylamine are added in the course of 5 minutes to a solution of 7 g of ethyl 2-(2-chloro-6,7,8-trifluoroquinoline-3-carb onyl)-3-dimethylamino-acrylate in 100 cm3 of trichloromethane kept at a temperature close to 20° C. and the mixture is stirred for a further 4 hours at this temperature. The reaction mixture is concentrated under reduced pressure (20 kPa) at about 50° C. The oily residue obtained is taken up in 100 cm3 of ethanol and 3 g of DBU. The mixture is heated to 80° C. and kept at this temperature, with stirring, for 1 hour and a half. After cooling to about 20° C., the insoluble matter is drained and washed with twice 30 cm3 of ethanol and twice 30 cm3 of diisopropyl ether. 4.5 g of 1-cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthridine are obtained in the form of a colourless solid melting at 260° C.

Workup

customclose to 20° C.
concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at about 50° C
customThe oily residue obtained
stirringwith stirring, for 1 hour
temperatureAfter cooling to about 20° C.
washwashed with twice 30 cm3 of ethanol and twice 30 cm3 of diisopropyl ether

Sources & evidence

ORD record: ord-09aaecc7b87642a085eedad35e221ef5
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04970213

Reaction notes

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