Water → HCID 13732607, compound

HRID 1731536Notes

Reaction equation

HRID 1731536 reaction equation
O.[Cl:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][N:6]=[C:5]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:4]=12>C1(C)C=CC=CC=1.O=[Mn]=O>[Cl:2][C:3]1[C:8]([CH:9]=[O:10])=[CH:7][N:6]=[C:5]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:4]=12

Participants

5

Reactant 2

HCID 962WaterHCID 20209064(4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methanol

Product 1

HCID 13732607HCID 13732607, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent2×

Procedure

Wet MnO2 (110 g) was refluxed for 90 minutes in 1 L of toluene with a Dean-stark trap for the separation of water. This suspension was then cooled and the 4-chloro-1-ethyl-1H-pyrazolo-[3,4-b]pyridine-5-methanol (17.5 g, 82.7 mmole) was added in 50 ml of toluene. The reaction mixture was then stirred for 6 hours and filtered with the aid of a filter pad. The toluene was evaporated and the residue added again to 100 g of wet MnO2 freshly prepared in the above manner. After additional 4 hours the reaction was briefly warmed at 55° and then filtered again through a filter pad. The residue which remained after evaporation of the toluene was purified by preparative high performance liquid chromatography (10% ethyl acetate/hexane, 250 ml/min) to yield 11.70 g of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxaldehyde, mp 89°-90° C.

Workup

  1. temperatureThis suspension was then cooled
  2. filtrationfiltered with the aid of a filter pad
  3. customThe toluene was evaporated
  4. additionthe residue added again to 100 g of wet MnO2
  5. customfreshly prepared in the above manner
  6. temperatureAfter additional 4 hours the reaction was briefly warmed at 55°
  7. filtrationfiltered again through a filter pad
  8. customafter evaporation of the toluene
  9. customwas purified by preparative high performance liquid chromatography (10% ethyl acetate/hexane, 250 ml/min)

Sources & evidence

ORD record
ord-b3c042ebecd448a68e2c6ec19ce593d7
Source dataset
uspto-grants-1986_11
Patent number
US04622326

Reaction notes

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