Sodium ethoxide → HCID 57717622, compound

HRID 1984386Notes

Reaction equation

HRID 1984386 reaction equation
[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[N:6]=[C:5]([C:12]#[N:13])[C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20]C(=O)C(C)(C)C)[CH3:2].[O-]CC.[Na+]>C(O)C>[CH2:1]([C:3]1[N:7]([CH2:8][CH2:9][CH2:10][CH3:11])[N:6]=[C:5]2[C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]=[C:12]2[NH2:13])[CH3:2]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 66958681HCID 66958681, compound

Product 1

HCID 57717622HCID 57717622, compoundYield 40.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of N-[2-(5-ethyl-1-butyl-3-cyano-1H-pyrazol-4-yl)phenyl]-2,2-dimethylpropanamide (0.45 g, 1.28 mmol) in ethanol (8 mL) was added sodium ethoxide in ethanol (21 wt % solution in ethanol, 1.03 g, 3.19 mmol). The solution was heated at reflux overnight, then was allowed to cool to ambient temperature. The solvent was removed under reduced pressure and the residue was triturated with water. A precipitate formed that was isolated by filtration and washed with water, then was purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform) to yield 0.14 g of 1-ethyl-2-butyl-2H-pyrazolo[3,4-c]quinolin-4-amine as a white crystalline solid, mp 215-216° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was triturated with water
  5. customA precipitate formed
  6. customthat was isolated by filtration
  7. washwashed with water
  8. customwas purified by chromatography on a HORIZON HPFC system (silica gel, gradient elution with 0-35% CMA in chloroform)

Sources & evidence

ORD record
ord-3aba8633fc604e0785da2bfa93d2585f
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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