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

HRID 1727870

반응식

HRID 1727870 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0d993d71c9dd4f9da18e2a28b9b43173
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495104B2

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