Dimethylformamide → N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine

HRID 2090236노트

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HRID 2090236 반응식
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1O)=[CH:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].CN(C=O)C.S(Cl)(Cl)=O.[Si:24]([O:31][CH2:32][CH2:33][CH2:34][NH2:35])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl.CCN(CC)CC>[Si:24]([O:31][CH2:32][CH2:33][CH2:34][NH:35][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])([C:27]([CH3:29])([CH3:30])[CH3:28])([CH3:26])[CH3:25]

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilaneHCID 178526762HCID 178526762, 화합물

생성물 1

HCID 68429388N-(3-(tert-Butyldimethylsilyloxy)propyl)-3-nitroquinolin-4-amine수율 91.5%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

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온도
0 °C

실험 절차

To a stirred solution of 3-nitro-quinolin-4-ol (5 g) in DCM (70 mL) was added DMF (2.3 mL) then thionyl chloride (2.1 mL) and the reaction mixture was refluxed for 3 h. The solution was cooled to 0° C. and 3-{[tert-butyl(dimethyl)silyl]oxy}propan-1-amine (6 g) was added followed by dropwise addition of Et3N (12 mL). The reaction mixture was stirred at rt for 2 h, then partitioned between DCM and saturated NaHCO3 solution. The organic layer was washed with water, dried, and the solvent evaporated under reduced pressure. The residue was triturated with iso-hexane to leave the subtitle compound (8.7 g).

후처리

  1. custompartitioned between DCM and saturated NaHCO3 solution
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent evaporated under reduced pressure
  5. customThe residue was triturated with iso-hexane

출처 및 근거

ORD 기록
ord-e9e810d5960d450b93f1a952b57f5c4e
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436178B2

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