Ethylamine → 8-Chloro-3-ethoxycarbonyl-1-ethyl-7-fluoro-4-oxo-1,4-dihydro-benzo[b][1,8]naphthyridine
Reaction equation
[CH2:1](N)C.Cl[C:5]1[C:14]([C:15]([C:17](=[CH:23][N:24](C)[CH3:25])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])=[CH:13][C:12]2[C:7](=[CH:8][C:9]([Cl:28])=[C:10]([F:27])[CH:11]=2)[N:6]=1.C1CCN2C(=NCCC2)CC1>C(O)C>[Cl:28][C:9]1[C:10]([F:27])=[CH:11][C:12]2[C:7]([CH:8]=1)=[N:6][C:5]1[N:24]([CH2:25][CH3:1])[CH:23]=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:15](=[O:16])[C:14]=1[CH:13]=2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Ethylamine (16 g) is added in the course of 5 minutes at between 10° and 15° C. to a stirred suspension of ethyl 2-(2,7-dichloro-6-fluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (13.5 g) in ethanol (135 cc), the temperature is allowed to rise to approximately 20° C., DBU (0.5 g) is added and the mixture is heated with stirring for 2 hours to a temperature in the region of 75° C. After cooling to a temperature in the region of 20° C., the precipitate is drained and washed with ethanol (2×100 cc) and ethyl ether (2×100 cc). 8-Chloro-3-ethoxycarbonyl-1-ethyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1, 8]naphthyridine (10.4 g) is obtained in the form of a yellow solid, m.p. 300°-301° C., which is used without further purification for the subsequent steps.
Workup
- customto rise to approximately 20° C.
- temperaturethe mixture is heated
- temperatureAfter cooling to a temperature in the region of 20° C.
- washwashed with ethanol (2×100 cc) and ethyl ether (2×100 cc)
Sources & evidence
- ORD record
- ord-57288882f2ba49acafa926d1cb4c08b8
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05053509
Reaction notes
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