Acetic Acid → HCID 135977936, compound

HRID 990597Notes

Reaction equation

HRID 990597 reaction equation
[I-].[OH:2][C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[C:5](=O)[CH2:6][N+]1C=CC=CC=1.[OH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=O)[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=1.C([O-])(=O)C.[NH4+:42].C(O)(=O)C>O>[OH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:26]=[C:27]([C:28]2[CH:33]=[CH:32][C:31]([N:34]([CH3:36])[CH3:35])=[CH:30][CH:29]=2)[CH:6]=[C:5]([C:4]2[CH:14]=[CH:15][CH:16]=[CH:17][C:3]=2[OH:2])[N:42]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 978474-(N,N-dimethylamino)-2'-hydroxychalconeHCID 517165Ammonium AcetateHCID 152701181-[2-(2-Hydroxyphenyl)-2-oxoethyl]pyridin-1-ium iodide

Product 1

HCID 135977936HCID 135977936, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.63 g (5 mmol) of 2-hydroxyphenacyl-pyridinium iodide, 0.53 g (2 mmol) of 1-(2-hydroxyphenyl)-3-(4-dimethylaminophenyl)-2-propen-1-one and 4 g of ammonium acetate were added to 4 ml of acetic acid, and the mixture was subjected to refluxing under heating for 5 hours. After being cooled to room temperature, the reaction mixture was poured to 50 ml of water and extracted two times with 30 ml each of chloroform. The chloroform was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography with chloroform as the eluent to obtain 0.61 g (yield: 79%) of 2,6-bis(2-hydroxyphenyl)-4-(4-dimethylaminophenyl)pyridine. (Incidentally in case where the reaction residue was subjected to re-crystallization from 30 ml of ethanol, the 2,6-bisphenolpyridine product was recovered at a yield of 64%.)

Workup

  1. temperatureto refluxing
  2. temperatureunder heating for 5 hours
  3. extractionextracted two times with 30 ml each of chloroform
  4. distillationThe chloroform was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-715a3b95c3314c63a92595f0fb7c48ee
Source dataset
uspto-grants-2002_10
Patent number
US06461749B2

Reaction notes

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