Ammonia → 2,4,6-Triphenylpyridine

HRID 918245

Reaction equation

HRID 918245 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[NH3:18]>C(O)(=O)C>[C:11]1([C:10]2[CH:2]=[C:1]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:2]=[C:1]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 240BenzaldehydeHCID 7410Acetophenone

Product 1

HCID 1363702,4,6-TriphenylpyridineYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

"Simple aldehydes and ketones without activating groups require mildly forcing conditions and produce the fully aromatic pyridines; accordingly, acetophenone, benzaldehyde, and ammonia in refluxing acetic acid gave a 68% yield of 2,4,6-triphenylpyridine and a 25% yield of β-phenylpropionophenone."

Sources & evidence

ORD record
ord-9efa448584b648dd916fdb58f7e36dd8
Source dataset
uspto-grants-1976_07
Patent number
US03970662

Linked notes

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