Methanol → HCID 17968814, compound

HRID 1760357Notes

Reaction equation

HRID 1760357 reaction equation
CO.[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=O)[CH3:13])[N:7]=1)(=O)[CH3:4].[CH3:15][C:16]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:17]=1[NH2:18]>C(O)=O>[CH3:15][C:16]1[CH:22]=[C:21]([CH3:23])[CH:20]=[CH:19][C:17]=1[N:18]=[C:3]([C:6]1[N:7]=[C:8]([C:12](=[N:18][C:17]2[CH:19]=[CH:20][C:21]([CH3:23])=[CH:22][C:16]=2[CH3:15])[CH3:13])[CH:9]=[CH:10][CH:11]=1)[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 72502,4-DimethylanilineHCID 707902,6-Diacetylpyridine

Product 1

HCID 17968814HCID 17968814, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

100 ml of methanol, 1.63 g of 2,6-diacetylpyridine (molecular weight 163.18; 10 mmols), and 4.84 g of 2,4-dimethylaniline (molecular weight 121.18; 40 mmols) were put into a 300 ml flask, and thoroughly stirred to prepare a homogeneous mixture. 0.6 ml of formic acid was added to this, and further the mixture was stirred for 12 hours to make the compounds reacted completely. The reaction mixture was left at −78° C. for 1 hour, and the resulting pale yellow crystal was taken out through filtration, washed with methanol, and dried under reduced pressure. Its 1H-NMR spectrum was assigned as the intended product, 2,6-diacetylpyridine-bis(2,4-dimethylphenylimine) (molecular weight 369.52; 1.60 g, 4.33 mmols, yield 43%).

Workup

  1. customto prepare a homogeneous mixture
  2. stirringwas stirred for 12 hours
  3. customreacted completely
  4. filtrationthe resulting pale yellow crystal was taken out through filtration
  5. washwashed with methanol
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-f062a079013d4e0993199251fd5aa60b
Source dataset
uspto-grants-2005_01
Patent number
US06841693B1

Reaction notes

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