Sodium → 3-butyryl-4-(2-methylphenylamino)-8-(3-(N-methyl-N-(3-phenylpropyl)amino)propoxy)quinoline

HRID 1090667ノート

反応式

HRID 1090667 の反応式
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[OH:24])(=[O:5])[CH2:2][CH2:3][CH3:4].[Na].OC1C=CC2C(=CC=CC=2)N=1.Cl.Cl[CH2:39][CH2:40][CH2:41][N:42]([CH3:52])[CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(O)C>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])=[CH:13][CH:12]=[CH:11][C:10]=2[O:24][CH2:39][CH2:40][CH2:41][N:42]([CH3:52])[CH2:43][CH2:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

参加物

6

反応物 4

HCID 5360545SodiumHCID 104037323-Butyryl-4-(2-methylphenylamino)8-hydroxyquinolineHCID 199136433-chloro-N-methyl-N-(3-phenylpropyl)-1-propylamine hydrochlorideHCID 178515546HCID 178515546、化合物

生成物 1

HCID 100520313-butyryl-4-(2-methylphenylamino)-8-(3-(N-methyl-N-(3-phenylpropyl)amino)propoxy)quinoline収率 31%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3-Butyryl-4-(2-methylphenylamino)-8-hydroxyquinoline (3.2 g, 10 mmol) was dried by azeotroping with toluene, then dissolved in dry ethanol (20 ml). Sodium (0.23 g, 10 mmol) was dissolved in ethanol (15 ml), and added to the hydroxyquinoline. The resulting solution was evaporated, and the solid redissolved in toluene (50 ml). 3-chloro-N-methyl-N-(3-phenylpropyl)-1-propylamine hydrochloride (1.5 g, 5.7 mmol) was added and the mixture heated at reflux under nitrogen for 3 hours. Evaporation of the solvent, chromatography (silica gel, 0-3% methanolic ammonia in chloroform) and crystallisation from ether gave 3-butyryl-4-(2-methylphenylamino)-8-(3-(N-methyl-N-(3-phenylpropyl)amino)propoxy)quinoline (0.9 g, 18%), m.p. 79°-81°.

後処理

  1. customby azeotroping with toluene
  2. dissolutiondissolved in dry ethanol (20 ml)
  3. customThe resulting solution was evaporated
  4. dissolutionthe solid redissolved in toluene (50 ml)
  5. temperaturethe mixture heated
  6. temperatureat reflux under nitrogen for 3 hours
  7. customEvaporation of the solvent, chromatography (silica gel, 0-3% methanolic ammonia in chloroform) and crystallisation from ether

出典と根拠

ORDレコード
ord-2e6d5430f55f4d2bac17d58f66bb06b3
出典データセット
uspto-grants-1992_01
特許番号
US05082841

反応ノート

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