4-Chloro-8-methoxy-2-methylquinoline → (rac)-1-(4-Chlorophenyl)-N*1*-(8-methoxy-2-methylquinolin-4-yl)-N*2*,N*2*-dimethylethane-1,2-diamine dihydrochloride

HRID 1966537

反応式

HRID 1966537 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]([NH2:27])[CH2:23][N:24]([CH3:26])[CH3:25])=[CH:18][CH:17]=1>C(OCC)(=O)C>[ClH:1].[ClH:15].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([CH:22]([NH:27][C:2]2[C:11]3[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:14])[CH:3]=2)[CH2:23][N:24]([CH3:25])[CH3:26])=[CH:20][CH:21]=1

参加物

4

反応物 2

HCID 8075834-Chloro-8-methoxy-2-methylquinolineHCID 16643575(2-Amino-2-(4-chlorophenyl)ethyl)dimethylamine

生成物 1

HCID 131730511(rac)-1-(4-Chlorophenyl)-N*1*-(8-methoxy-2-methylquinolin-4-yl)-N*2*,N*2*-dimethylethane-1,2-diamine dihydrochloride収率 60.4%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

4-Chloro-8-methoxy-2-methylquinoline (2.00 g, 9.63 mmole), 1-(4-chlorophenyl)N*2*,N*2*-dimethylethane-1,2-diamine (2.30 g, 11.6 mmole), sodium tert-butylate (1.3 g, 13.5 mmole), tris(dibenzylidenaceton)-dipalladium(0) (0.18 g, 0.193 mmole) and 2-dicyclohexyl-phosphino-2(N,N-dimethylamino)biphenyl (0.27 g, 0.674 mmole) were stirred at 150° C. under nitrogen atmosphere in a microwave oven for 30 min. The reaction mixture was dissolved in ethyl acetate and filtered. The filtrate was extracted with water. The organic phases were dried, concentrated and the residue was purified using silica gel chromatography, eluting with dichloromethane:methanol 90:10. Precipitation in isopropanol/HCl and in ethyl acetate gave the product (1.55 g, 36%).

後処理

  1. filtrationfiltered
  2. extractionThe filtrate was extracted with water
  3. customThe organic phases were dried
  4. concentrationconcentrated
  5. customthe residue was purified
  6. washeluting with dichloromethane:methanol 90:10
  7. customPrecipitation in isopropanol/HCl

出典と根拠

ORDレコード
ord-12c7456afd1f4763b019a5b648c41308
出典データセット
uspto-grants-2013_04
特許番号
US08420670B2

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