Hydrochloric Acid → 4-chloro-1'H-[2,2';6',2'']terpyridin-4'-one

HRID 1726854Notes

Reaction equation

HRID 1726854 reaction equation
[OH-].[NH4+:2].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](=O)[CH2:11][C:12](=[O:22])[CH2:13][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=O)[CH:5]=1.Cl>C(O)(C)C>[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]2[NH:2][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:13][C:12](=[O:22])[CH:11]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 575649861-(4-Chloropyridin-2-yl)-5-(pyridin-2-yl)pentane-1,3,5-trione

Product 1

HCID 575649954-chloro-1'H-[2,2';6',2'']terpyridin-4'-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

110 ml of 25 per cent strength ammonium hydroxide solution are added to 1-(4-chloropyridin-2-yl)-5-pyridin-2-ylpentane-1,3,5-trione obtained as described above in 100 ml of isopropanol and the mixture is boiled under reflux for 4.5 hours. At room temperature, the pH is brought to 5 with 6N hydrochloric acid and the mixture is filtered. The residue is filtered through silica gel (eluent: chloroform/methanol/ammonium hydroxide solution 4:1:0.1) and evaporated. After recrystallization from acetone, 4-chloro-1′H-[2,2′;6′,2″]terpyridin-4′-one is obtained as a grey solid which is processed further without any particular purification steps. 1H-NMR (360 MHz, DMSO-de): 8.728.63 (m, 2H); 8.62-8.53 (m, 2H); 7.98 (ddd, 1H, J=7.7,7.7,1.8 Hz); 7.87 (d, 1H, J=2.2 Hz); 7.83 (d, 1H, J=2.2 Hz); 7.59 (dd, 1H, J=5.4,2.2 Hz); 7.43-7.51 (m, 1H); 2.07 (s, 1 H).

Workup

  1. customobtained
  2. temperatureunder reflux for 4.5 hours
  3. customAt room temperature
  4. filtrationthe mixture is filtered
  5. filtrationThe residue is filtered through silica gel (eluent: chloroform/methanol/ammonium hydroxide solution 4:1:0.1)
  6. customevaporated
  7. customAfter recrystallization from acetone

Sources & evidence

ORD record
ord-d3a2537595de4cbcbdffb4dfa88a2f7c
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

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