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(R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol → (R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol

HRID 2277391
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HRID 2277391 반응식
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][C@H:21]([OH:23])[CH3:22])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.C(O[K])=O>C1COCC1.O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH2:20][C@H:21]([OH:23])[CH3:22])=[CH:16][CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:24][CH:25]=1
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참가 물질

5

반응물 2

HCID 68193961(R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-olHCID 178526052HCID 178526052, 화합물

생성물 1

HCID 68193946(R)-1-((4-(4-aminophenoxy)quinolin-7-yl)oxy)propan-2-ol수율 76.2%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21881883Oxolane--water (1/1)용매

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온도
73 °C

실험 절차

To a suspension of (R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol (3.6 g, 10.6 mmol) and HCOOK (6.2 g, 74.1 mmol) in THF/H2O (33 mL/11 mL) was added a catalytic amount of 10% Pd/C (33 mg). After stirring at 73° C. for 5 hours, the reaction mixture was cooled to room temperature. The mixture was filtered through a celite pad and the filter cake was washed with DCM (50 mL). The organic phase was separated, dried over Na2SO4, and concentrated in vacuo. The residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1) to give the title compound as a yellow solid (2.5 g, 76.2%).

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. filtrationThe mixture was filtered through a celite pad
  3. washthe filter cake was washed with DCM (50 mL)
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a column chromatography on silica gel (EtOAc/PE=1:1)

출처 및 근거

ORD 기록
ord-1e9fc707e9e2418186508247857643ad
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133162B2

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