Sodium Iodide → Bispyridyl-anthracene

HRID 265221노트

반응식

HRID 265221 반응식
NC1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22]Cl.[I-].[Na+].[CH:26](N(CC)C(C)C)([CH3:28])[CH3:27].[C:35](#[N:37])[CH3:36]>>[N:37]1[CH:28]=[CH:26][CH:27]=[CH:36][C:35]=1[C:9]1[C:10]2[C:11]([C:22]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]=3)=[C:7]3[C:8]=1[CH:3]=[CH:4][CH:5]=[CH:6]3)=[CH:12][CH:13]=[CH:14][CH:15]=2

참가 물질

6

반응물 5

HCID 5238Sodium IodideHCID 6342AcetonitrileHCID 130699-AminoanthraceneHCID 23393Picolyl chlorideHCID 81531Diisopropylethylamine

생성물 1

HCID 101263369Bispyridyl-anthracene수율 83%

실험 절차

A solution of 9-aminoanthracene (1.0 g, 5.1 mmoles) in 20 mL acetonitrile is combined with 2-picolyl chloride (2.0 g, 12.7 moles), sodium iodide (0.9 g, 6 mmoles) and N,N-diisopropylethylamine (2.8 g, 20.4 mmoles and the resulting solution is heated at reflux for 16 hours. The resulting dark solution is evaporated and crystallized from 30 mL methanol to give the bispyridyl-anthracene as a dark solid (1.6 g, 83% yield). Using completely analogous methods, other fluorescent bis-pyridyl indicators can be synthesized starting with a variety of amine-containing fluorescent dyes, such as 7-aminocoumarin-4-acetic acid and 1-aminopyrene.

후처리

  1. temperaturethe resulting solution is heated
  2. temperatureat reflux for 16 hours
  3. customThe resulting dark solution is evaporated
  4. customcrystallized from 30 mL methanol

출처 및 근거

ORD 기록
ord-c383143f592e4b9daeb46b93fcebb922
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648270

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