Water → (4-Tert-butylcyclohexyl)-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]amine

HRID 1727870ノート

反応式

HRID 1727870 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.[C:23]([CH:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)([CH3:26])([CH3:25])[CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>CN(C)C=O.C(OCC)(=O)C>[C:23]([CH:27]1[CH2:32][CH2:31][CH:30]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][CH:18]=2)[CH2:29][CH2:28]1)([CH3:26])([CH3:25])[CH3:24]

参加物

7

反応物 4

HCID 962WaterHCID 73924-tert-ButylcyclohexanoneHCID 5049666Sodium triacetoxyborohydrideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

生成物 1

HCID 10113795(4-Tert-butylcyclohexyl)-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]amine収率 11.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

4-(6,7-Dimethoxy-4-quinolyloxy)aniline (300 mg) was dissolved in N,N-dimethylformamide (10 ml) to prepare a solution. 4-Tert-butylcyclohexanone (200 mg) was then added to the solution, and the mixture was stirred at 60° C. for one hr. The reaction solution was cooled to room temperature before sodium triacetoxy borohydride (400 mg) was added thereto. The mixture was then stirred at room temperature for 3 hr. Water and ethyl acetate were added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (50 mg, yield 11%).

後処理

  1. customto prepare a solution
  2. additionwas added
  3. stirringThe mixture was then stirred at room temperature for 3 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. customThe solvent was removed by evaporation under the reduced pressure
  8. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-0d993d71c9dd4f9da18e2a28b9b43173
出典データセット
uspto-grants-2009_02
特許番号
US07495104B2

反応ノート

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