Ammonia → HCID 58781425, compound

HRID 1726857Notes

Reaction equation

HRID 1726857 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=O)[CH2:9][C:10](=[O:21])[CH2:11][C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=2)=O)[CH:3]=1.[NH3:23]>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[NH:23][C:12]([C:14]3[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][N:15]=3)=[CH:11][C:10](=[O:21])[CH:9]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 17971929HCID 17971929, compound

Product 1

HCID 58781425HCID 58781425, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
4 °C

Procedure

38.5 g (0.114 mol) of 1,5-bis(4-chloropyridin-2-yl)pentane-1,3,5-trione are suspended in 1.25 l of 2-propanol. A total of 230 ml of 25% (w/w) ammonia solution is added at 60° C.-70° C. over the course of five and a half hours. The mixture is cooled to 4° C. and the whitish 4,4″-dichloro-1′H-[2,2′;6′,2″]terpyridin-4′-one formed is filtered off. 1H-NMR (360 MHz, DMSO-d6): 8.65 (d, 2H, J=5.4 Hz); 8.57 (d, 2H, J=2.2 Hz); 7.82 (s, 2H); 7.59 (dd, 2H, J=5.4,2.2 Hz).

Sources & evidence

ORD record
ord-98b07e0ed3e344c78eb0496e6ca0ea21
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

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