Ethanol → HCID 178508016, compound

HRID 1943919Notes

Reaction equation

HRID 1943919 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:12]([CH2:13][OH:14])=[N:11][NH:10][C:7]2=[N:8][CH:9]=1)([O-])=O.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:12]([CH2:13][OH:14])=[N:11][NH:10][C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 178526795HCID 178526795, compound

Product 1

HCID 178508016HCID 178508016, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A sealed microwave vial was charged with (5-nitro-1H-pyrazolo[3,4-b]pyridin-3-yl)methanol (0.10 g, 0.515 mmol), iron (0.345 g, 6.18 mmol), ammonium chloride (0.110 g, 2.06 mmol) and ethanol:water (2.25 mL, 4:1). The mixture was heated in a microwave reactor at 110° C. for 20 minutes. The reaction mixture was filtered through a pad of celite. The filtrate was diluted with ethyl acetate and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo to afford crude (5-amino-1H-pyrazolo[3,4-b]pyridin-3-yl)methanol that was used into the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×)
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-64018a0224c4410c86864552e1b06c9e
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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