Potassium Hydroxide → HCID 66626967, compound

HRID 1970706Notes

Reaction equation

HRID 1970706 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[K+].I[CH2:19][CH2:20][CH3:21]>CN(C)C=O>[CH3:1][C:2]1[N:7]=[C:6]([N:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)[CH2:19][CH2:20][CH3:21])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 336431-IodopropaneHCID 30210056-Methyl-N-(6-methyl-2-pyridyl)pyridin-2-amine

Product 1

HCID 66626967HCID 66626967, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 1.0 g 6-methyl-N-(6-methylpyridin-2-yl)pyridin-2-amine, 0.84 g of pulverized potassium hydroxide and 15 ml of N,N-dimethylformamide. After stirring for 1 hour under nitrogen, the mixture was cooled to 5 C and 0.85 g of 1-iodopropane were added. The mixture was allowed to warm to 22 C and stirred for 16 hours. After quenching with 15 ml water, the product was extracted twice with diethyl ether and washed with water. Following removal of solvent, the product was purified by silica gel chromatography using 10% ethyl acetate in hexane to give 1.0 g of a colorless oil.

Workup

  1. additionwere added
  2. temperatureto warm to 22 C
  3. stirringstirred for 16 hours
  4. customAfter quenching with 15 ml water
  5. extractionthe product was extracted twice with diethyl ether
  6. washwashed with water
  7. customremoval of solvent
  8. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c1bbf017eade4d2793012f2985559f53
Source dataset
uspto-grants-2013_04
Patent number
US08431045B2

Reaction notes

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