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2-Methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol → 1-((4-(4-Aminophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol

HRID 2277385
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HRID 2277385 반응식
[CH3:1][C:2]([OH:26])([CH3:25])[CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1.C(O[K])=O>O.C1COCC1.[Pd]>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][C:9]2[C:8]3[C:13](=[CH:14][C:5]([O:4][CH2:3][C:2]([CH3:25])([OH:26])[CH3:1])=[CH:6][CH:7]=3)[N:12]=[CH:11][CH:10]=2)=[CH:17][CH:18]=1
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참가 물질

6

반응물 2

HCID 681942572-Methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-olHCID 178526052HCID 178526052, 화합물

생성물 1

HCID 681939811-((4-(4-Aminophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol수율 97.7%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매

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온도
45 °C

실험 절차

To a solution of 2-methyl-1-((4-(4-nitrophenoxy)quinolin-7-yl)oxy)propan-2-ol (2.8 g, 7.9 mmol) and HCOOK (4.6 g, 55.3 mmol) in water (4 mL) and THF (12 mL) was added 10% Pd/C (0.24 g). The reaction mixture was stirred at 45° C. for 21 hours and then cooled to room temperature. The mixture was filtered through a Celite pad. The organic phase was separated and washed with brine (20 mL). The aqueous phase was extracted with EtOAc (15 mL). The combined organic phases were concentrated in vacuo and the residue was dried in vacuo at 50° C. overnight to give the title compound as a yellow solid (2.5 g, 97.7%).

후처리

  1. temperaturecooled to room temperature
  2. filtrationThe mixture was filtered through a Celite pad
  3. customThe organic phase was separated
  4. washwashed with brine (20 mL)
  5. extractionThe aqueous phase was extracted with EtOAc (15 mL)
  6. concentrationThe combined organic phases were concentrated in vacuo
  7. customthe residue was dried in vacuo at 50° C. overnight

출처 및 근거

ORD 기록
ord-c9929c7fd4d24b6aa7c03dc44f7ed618
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133162B2

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