Potassium Iodide → 3-(Quinolin-4-yloxy)propan-1-ol

HRID 40797

反応式

HRID 40797 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Cl[CH2:21][CH2:22][CH2:23][OH:24]>CN(C=O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([O:11][CH2:21][CH2:22][CH2:23][OH:24])=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 178516385quinolin-4-ol

生成物 1

HCID 685762503-(Quinolin-4-yloxy)propan-1-ol収率 28%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

A suspension of quinolin-4-ol (1.35 g, 9.30 mmol), anhydrous potassium carbonate (3.73 g, 26 mmol) and potassium iodide (4.23 g) in anhydrous DMF (8 mL) was stirred at 25° C. for 30 minutes. 3-Chloropropanol (2.93 g, 31 mmol) was added and the reaction was stirred until the starting material was consumed. The reaction was diluted with dichloromethane and extracted with water. The product was obtained as a slightly yellow solid (0.5298 g, 28%) after evaporation of the dichloromethane layer, and was used for the next step without further purification. 1H NMR (400 MHz, CDCl3): 2.09 (2H, m), 3.93 (2H, t, J=5.6 Hz), 4.10 (2H, t, J=5.6 Hz), 4.51 (11H, s), 6.25 (1H, d, J=5.5 Hz), 7.32 (1H, t, J=7.4 Hz), 7.56 (1H, t, J=8.2 Hz), 7.90 (1H, d, J=8.4 Hz), 7.93 (1H, d, J=8.4 Hz), 8.36 (1H, d, J=5.3 Hz).

後処理

  1. stirringthe reaction was stirred until the starting material
  2. customwas consumed
  3. additionThe reaction was diluted with dichloromethane
  4. extractionextracted with water

出典と根拠

ORDレコード
ord-d91781c33a6f4b49b78e7d1ae719acf2
出典データセット
uspto-grants-2013_09
特許番号
US08530491B2

関連ノート

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