Sodium Iodide → Bispyridyl-anthracene

HRID 849652Notes

Reaction equation

HRID 849652 reaction equation
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

Participants

6

Reactant 5

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

Product 1

HCID 101263369Bispyridyl-anthraceneYield 83%

Procedure

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 mmoles), 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.

Workup

  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

Sources & evidence

ORD record
ord-ef236f58298c44b8802395181124d7c2
Source dataset
uspto-grants-2000_01
Patent number
US06013802

Reaction notes

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