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

HRID 1452781

반응식

HRID 1452781 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
90 °C

실험 절차

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.

후처리

  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%

출처 및 근거

ORD 기록
ord-7c5a8585840943639998021c9e2c21f8
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07473779B2

연결된 노트

불러오는 중…