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

HRID 1090667노트

반응식

HRID 1090667 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-2e6d5430f55f4d2bac17d58f66bb06b3
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082841

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