Sodium ethoxide → HCID 57717622, compound

HRID 2283786Notes

Reaction equation

HRID 2283786 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-a03c14c8906c475bb1f9e248af2e8e14
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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