Hydrazine → 4'-Hydrazino-2,2':6',2''-terpyridine

HRID 640666Notes

Reaction equation

HRID 640666 reaction equation
[NH2:1][NH2:2].Cl[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[N:7]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:5]=1>CC(O)CC>[N:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:8]1[CH:9]=[C:4]([NH:1][NH2:2])[CH:5]=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 6677484'-Chloro-2,2':6',2''-terpyridine

Product 1

HCID 105394884'-Hydrazino-2,2':6',2''-terpyridine

Reagents, catalysts & solvents 1

HCID 6568(+-)-2-ButanolSolvent

Procedure

4 ml (126 mmol) of hydrazine are added to 600 mg (2.2 mmol) of 4′-chloro-[2,2′;6′,2″]-terpyridine in 12 ml of 2-butanol. The mixture is heated at reflux for 17 hours and cooled, and [2,2′;6′,2″]terpyridin-4′-yl-hydrazine is filtered off in the form of a white solid. 1H-NMR (360 MHz, DMSO-d6): 4.38 (s br, 2H); 7.38-7.45 (m, 2H); 7.84 (s, 2H); 7.88-7.97 (m, 3H); 8.52-8.57 (m, 2H); 8.64-8.76 (m, 2H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 17 hours
  3. temperaturecooled
  4. filtration[2,2′;6′,2″]terpyridin-4′-yl-hydrazine is filtered off in the form of a white solid

Sources & evidence

ORD record
ord-6d718f3c4d304d179a0e089a1602b62b
Source dataset
uspto-grants-2010_04
Patent number
US07692004B2

Reaction notes

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