Acetophenone → Benzenamine, 4-(2,6-diphenyl-4-pyridinyl)-N,N-dimethyl-

HRID 1287548Notes

Reaction equation

HRID 1287548 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=O)[CH3:13].[C:21]([O-])(=O)[CH3:22].[NH4+:25]>C(O)(=O)C>[C:3]1([C:21]2[CH:22]=[C:7]([C:6]3[CH:9]=[CH:10][C:3]([N:2]([CH3:11])[CH3:1])=[CH:4][CH:5]=3)[CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:25]=2)[CH:10]=[CH:9][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 74794-(Dimethylamino)BenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 93126Benzenamine, 4-(2,6-diphenyl-4-pyridinyl)-N,N-dimethyl-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

75 parts of p-dimethylaminobenzaldehyde and 125 parts of acetophenone together with 500 parts of ammonium acetate are heated in 1,000 parts of glacial acetic acid for four hours under reflux. The precipitate deposited after standing for twelve hours at room temperature is suction filtered and recrystallized from 500 parts of ethanol. 57 parts of a pale yellow compound (2,6-diphenyl-4-(4'-dimethylaminophenyl)-pyridine) is obtained which has a melting point of 128° to 129° C.

Workup

  1. temperatureunder reflux
  2. waitafter standing for twelve hours at room temperature
  3. filtrationfiltered
  4. customrecrystallized from 500 parts of ethanol

Sources & evidence

ORD record
ord-badc0423e2924a79b39b5765ab417922
Source dataset
uspto-grants-1976_10
Patent number
US03985376

Reaction notes

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