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

HRID 2090236ノート

反応式

HRID 2090236 の反応式
[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]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11074190(3-Aminopropoxy)(tert-butyl)dimethylsilaneHCID 178526762HCID 178526762、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e9e810d5960d450b93f1a952b57f5c4e
出典データセット
uspto-grants-2013_05
特許番号
US08436178B2

反応ノート

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