Ethanol → HCID 16791219, compound

HRID 476035Notes

Reaction equation

HRID 476035 reaction equation
[CH3:1][C:2]1[CH:3]=C(C#N)[C:5]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1.[OH-:20].[Na+].[CH2:22]([OH:24])[CH3:23]>O>[CH3:1][C:2]1[CH:3]=[C:23]([C:22]([OH:20])=[O:24])[C:5]2[CH:10]=[N:9][N:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67124107HCID 67124107, compound

Product 1

HCID 16791219HCID 16791219, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-Methyl-1-(phenylmethyl)-1H-pyrazolo[3,4-b]pyridine-4-carbonitrile (1 g), sodium hydroxide (0.805 g, 20.14 mmol), ethanol (25 mL) and water (10 mL) were heated at reflux for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The crude product was suspended in water (50 mL) and acidified by dropwise addition of 6N HCl. The solid product was filtered off and dissolved in 100 ml of EtOAc. The solution dried over MgSO4, filtered, and concentrated in vacuo. The final product was obtained as 0.730 g. LCMS E-S (M+H)=267.9. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.71 (s, 3H), 5.70 (s, 2H), 7.15-7.37 (m, 5H), 7.63 (s, 1H), 8.33 (s, 1H), 13.86 (s, 1H).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent was removed under reduced pressure
  3. additionacidified by dropwise addition of 6N HCl
  4. filtrationThe solid product was filtered off
  5. dissolutiondissolved in 100 ml of EtOAc
  6. dry with materialThe solution dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3627a8be69134d6185c564d51b50528f
Source dataset
uspto-grants-2014_01
Patent number
US08637509B2

Reaction notes

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