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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
ノート
印刷プレビュー

反応式

HRID 2277391 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 68193961(R)-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-olHCID 178526052HCID 178526052、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
73 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-1e9fc707e9e2418186508247857643ad
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133162B2

反応ノート

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