Isopropanol → 2-(Methyl-[2,2';6'2'']terpyridine-4'yl-amino)-ethanol

HRID 273306

反応式

HRID 273306 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1.[CH3:20][NH:21][CH:22](O)[CH3:23].C([OH:28])(C)C>ClCCl.O.O.O.O.[Fe](Cl)Cl>[CH3:20][N:21]([C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH:3]=1)[CH2:22][CH2:23][OH:28]

参加物

6

反応物 3

HCID 3776IsopropanolHCID 6677484'-Chloro-2,2':6',2''-terpyridineHCID 5247031N-Methylaminoethanol

生成物 1

HCID 104948702-(Methyl-[2,2';6'2'']terpyridine-4'yl-amino)-ethanol

試薬・触媒・溶媒 2

HCID 16211588Ferrous chloride tetrahydrate触媒HCID 6344Dichloromethane溶媒

実験手順

A solution in 20 ml of dichloromethane of 1.61 g (6 mmol) of 4′-chloro-2,2′:6′,2″-terpyridine and 20 ml of N-methylaminoethanol are added in succession to a solution of 1.35 g (6.8 mmol) of iron(II) chloride tetrahydrate in 100 ml of isopropanol. The mixture is then boiled at reflux for 20 hours. The mixture is concentrated and a solution of 1.66 g of ammonium hexafluorophosphate in 10 ml of methanol is added. The resulting violet precipitate is washed four times using 50 ml of diethyl ether each time and once with 50 ml of water. The residue is then stirred for 14 hours in a solution of 4 g of sodium hydroxide in 300 ml of water/acetonitrile (1:1 v/v) in an oxygen atmosphere. Filtration is carried out over kieselguhr and the residue is washed with 50 ml of water, 50 ml of acetonitrile and 100 ml of dichloromethane. The filtrates are concentrated. Extraction is carried out four times with dichloromethane and the combined organic extracts are dried over sodium sulfate, filtered and concentrated. The residue is recrystallised from acetone/petroleum ether and acetonitrile; 2-(methyl-[2,2′;6′,2″]terpyridin-4′-yl-amino)-ethanol is obtained in the form of a white solid. MS (ESI pos., KF), m/z=345 (100, [M+K]+); 307 (35, [M+H]+).

後処理

  1. temperatureat reflux for 20 hours
  2. concentrationThe mixture is concentrated
  3. additiona solution of 1.66 g of ammonium hexafluorophosphate in 10 ml of methanol is added
  4. washThe resulting violet precipitate is washed four times
  5. filtrationFiltration
  6. washthe residue is washed with 50 ml of water, 50 ml of acetonitrile and 100 ml of dichloromethane
  7. concentrationThe filtrates are concentrated
  8. extractionExtraction
  9. dry with materialthe combined organic extracts are dried over sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is recrystallised from acetone/petroleum ether and acetonitrile

出典と根拠

ORDレコード
ord-7f83369338ac47dcbb74637202ddd29b
出典データセット
uspto-grants-2008_11
特許番号
US07456285B2

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