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

HRID 344896Notes

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.C(O)C.C1CCN2C(=NCCC2)CC1>ClC(Cl)Cl>[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

Cyclopropylamine (4.12 g) is added in the course of 5 minutes to a solution, maintained at a temperature in the region of 20° C., of ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (7 g) in trichloromethane (100 cc), and the mixture is stirred for a further 4 hours at the same temperature. The reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 50° C. The oily residue obtained is taken up with ethanol (100 cc) and DBU (3 g). The mixture is heated to 80° C. and kept stirring at the same temperature for 1 hour and a half. After cooling to approximately 20° C., the insoluble matter is drained and washed with ethanol (2×30 cc) and isopropyl ether (2×30 cc). 1-Cyclopropyl-3-ethoxycarbonyl-7,8,9-trifluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (4.5 g) is obtained in the form of a colorless solid, m.p. 260° C.

Workup

concentrationThe reaction mixture is concentrated under reduced pressure (20 kPa) at approximately 50° C
customThe oily residue obtained
stirringkept stirring at the same temperature for 1 hour
temperatureAfter cooling to approximately 20° C.
washwashed with ethanol (2×30 cc) and isopropyl ether (2×30 cc)

Sources & evidence

ORD record: ord-aa9c30ce7d314705b014427735207341
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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