Ammonia → HCID 178463021, compound

HRID 262283Notes

Reaction equation

HRID 262283 reaction equation
C([O:3][C:4]([C:6]1[C:7]([OH:17])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=O)C.[NH3:18]>CN(C)C=O>[CH2:15]([N:12]1[C:9]2=[N:10][CH:11]=[C:6]([C:4]([NH2:18])=[O:3])[C:7]([OH:17])=[C:8]2[CH:14]=[N:13]1)[CH3:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178469631HCID 178469631, compound

Product 1

HCID 178463021HCID 178463021, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.8 g. of ethyl-1-ethyl-4-hydroxy-1H-pyrazolo-[3,4-b]pyridine-5-carboxylate (J. Het. Chem., supra) (0.029 mol.) and 100 ml. of ammonia in dimethylformamide (48 g. NH3 /1; cooled at 4°) are filled into a steel autoclave. The mixture is heated to 150° for 6 hours. After cooling, the solution is evaporated to dryness and the residue is treated with ether. The 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxamide is used in the next step without further purification. A sample, recrystallized from ethanol, melts at 267°-268° (dec.), yield 3.6 g. (60%).

Workup

  1. temperatureThe mixture is heated to 150° for 6 hours
  2. temperatureAfter cooling
  3. customthe solution is evaporated to dryness
  4. additionthe residue is treated with ether
  5. customThe 1-ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxamide is used in the next step without further purification
  6. customA sample, recrystallized from ethanol, melts at 267°-268° (dec.), yield 3.6 g

Sources & evidence

ORD record
ord-af3df136ef90404381098c13e1f77281
Source dataset
uspto-grants-1979_05
Patent number
US04153796

Reaction notes

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