4-Nitrophenol → 2-[(4-Nitrophenoxy)methyl]quinoline

HRID 1452781

反応式

HRID 1452781 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

参加物

5

反応物 3

HCID 9804-NitrophenolHCID 203942-(Chloromethyl)quinolineHCID 24758Sodium hydride

生成物 1

HCID 137703602-[(4-Nitrophenoxy)methyl]quinoline収率 75%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
90 °C

実験手順

0.4 g (11 mmole) of 60% NaH is introduced into a flask containing 25 ml of anhydrous DMF under an argon atmosphere. A solution of 1.38 g (10 mmole) of 4-nitrophenol in 5 ml of anhydrous DMF is added dropwise, under agitation at 23° C. After 30 minutes a solution of 1.77 g (10 mmole) of 2-(chloromethyl)-quinoline in 5 ml of anhydrous DMF is added dropwise and agitation is continued for 15 hours while heating the mixture at 90° C. At the end of the reaction, the mixture is poured onto ice and an abundant precipitate forms. The suspension is filtered, rinsed twice with 25 ml of water followed by 20 ml of ethyl ether. A white solid is thus obtained with a yield of 75%. Melting point: 154-155° C.

後処理

  1. customAt the end of the reaction
  2. additionthe mixture is poured onto ice
  3. filtrationThe suspension is filtered
  4. washrinsed twice with 25 ml of water
  5. customA white solid is thus obtained with a yield of 75%

出典と根拠

ORDレコード
ord-7c5a8585840943639998021c9e2c21f8
出典データセット
uspto-grants-2009_01
特許番号
US07473779B2

関連ノート

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