Ethanol → 4-(2,6-Diphenylpyridin-4-yl)aniline

HRID 582022Notes

Reaction equation

HRID 582022 reaction equation
[OH-].[Na+].C(O)C.C([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:19]=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:17]=2)=[CH:12][CH:11]=1)(=O)C>O>[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[C:18]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:19]=[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:21]=2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53879234HCID 53879234, compound

Product 1

HCID 543405974-(2,6-Diphenylpyridin-4-yl)anilineYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1.50 g of sodium hydroxide, 100 ml of ethanol and 10 ml of water were added to 1.50 g of 4-(4-acetamidophenyl)-2,6-diphenylpyridine obtained on the basis of Reference Example 2 as a reference, and the mixture was refluxed for 46 hours. After cooling, 100 ml of water was added thereto, and the resulting product was recovered therefrom by filtration. By recrystallization from ethanol, 1.17 g of the captioned compound was obtained.

Workup

  1. customobtained on the basis of Reference Example 2 as a reference
  2. temperaturethe mixture was refluxed for 46 hours
  3. temperatureAfter cooling
  4. customthe resulting product was recovered
  5. filtrationby filtration
  6. customBy recrystallization from ethanol

Sources & evidence

ORD record
ord-18377e13c9f04de49b5a696b1bf354ce
Source dataset
uspto-grants-1999_07
Patent number
US05922743

Reaction notes

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