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

HRID 344883ノート

反応式

HRID 344883 の反応式
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]

参加物

5

反応物 3

HCID 6329MethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53994177Ethyl 2-(2-chloro-6,7,8-trifluoro-3-quinolinecarbonyl)(dimethylamino)acrylate

生成物 1

HCID 194236883-Ethoxycarbonyl-7,8,9-trifluoro-1-methyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine収率 79.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
30 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-5273737eea94405b9e55784987283210
出典データセット
uspto-grants-1991_10
特許番号
US05053509

反応ノート

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