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

HRID 2245183Notes

Reaction equation

HRID 2245183 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[N:14]=2)[CH:8]=1>CC(O)(CC)C.[Cl-].[Zn+2].[Cl-]>[CH3:1][N:2]([C:17]1[CH:16]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:14]=[C:13]([C:9]2[CH:8]=[CH:7][CH:12]=[CH:11][N:10]=2)[CH:18]=1)[CH2:3][CH2:4][OH:5]

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 158614074'-Chloro-2,2';6,2''-terpyridine

Product 1

HCID 104948702-(Methyl-[2,2';6'2'']terpyridine-4'yl-amino)-ethanolYield 84.5%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 64052-Methyl-2-butanolSolvent

Procedure

129 g (1.72 mol) 2-methylamino-ethanol and 390 mg (2.86 mmol) zinc(II)-chloride are successively added to a suspension of 15.3 g (57.2 mmol) 4′-chloro-2,2′;6,2″-terpyridine in 100 ml 2-methyl-2-butanol. The reaction mixture is refluxed for 2.5 days. A brown suspension is obtained, which is evaporated under vacuum to a yellow-brown solid product. 100 ml water is added to this product and stirred at room temperature for 20 minutes. Then, the obtained mixture is filtrated and the filter residue dried for 12 hours at (45° C., 10 mbar). 14.8 g (84%) of 2-(methyl-[2,2′;6′2″]terpyridine-4′yl-amino)-ethanol as colourless solid product is obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 2.5 days
  2. customA brown suspension is obtained
  3. customwhich is evaporated under vacuum to a yellow-brown solid product
  4. addition100 ml water is added to this product
  5. filtrationThen, the obtained mixture is filtrated
  6. customthe filter residue dried for 12 hours at (45° C., 10 mbar)

Sources & evidence

ORD record
ord-d059e1d43ad049189646d43be0908f26
Source dataset
uspto-grants-2010_03
Patent number
US07682404B2

Reaction notes

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