Methylamine → 3-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine

HRID 344883Notes

Reaction equation

CN.Cl[C:4]1[C:13]([C:14]([C:16](=[CH:22][N:23]([CH3:25])C)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:15])=[CH:12][C:11]2[C:6](=[C:7]([F:28])[C:8]([F:27])=[C:9]([F:26])[CH:10]=2)[N:5]=1.C1CCN2C(=NCCC2)CC1>C(O)C>[CH2:20]([O:19][C:17]([C:16]1[C:14](=[O:15])[C:13]2[CH:12]=[C:11]3[CH:10]=[C:9]([F:26])[C:8]([F:27])=[C:7]([F:28])[C:6]3=[N:5][C:4]=2[N:23]([CH3:25])[CH:22]=1)=[O:18])[CH3:21]

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of approximately 5° C. of methylamine (10 g) in ethanol (50 cc) is added in the course of 10 minutes at between 5° and 10° C. to a suspension, maintained at a temperature in the region of 5° C., of ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)-3-(dimethylamino)acrylate (19.3 g) in ethanol (150 cc), the mixture is stirred for 1 hour at between 5° and 10° C. and the temperature is allowed to rise to approximately 20° C. The solution obtained is treated with DBU (7.6 g) and heated to approximately 30° C. for 1 hour. After cooling to a temperature in the region of 20° C., the product is drained and washed with ethanol (2×100 cc) and isopropyl ether (2×100 cc). 3-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine (13.4 g) is obtained in the form of a yellow solid, m.p. 320° C., which is used without further purification for the subsequent steps.

Workup

customto rise to approximately 20° C
customThe solution obtained
temperatureAfter cooling to a temperature in the region of 20° C.
washwashed with ethanol (2×100 cc) and isopropyl ether (2×100 cc)

Sources & evidence

ORD record: ord-5273737eea94405b9e55784987283210
Source dataset: uspto-grants-1991_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05053509

Reaction notes

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