Hydrazine → HCID 178468518, compound

HRID 1526114Notes

Reaction equation

HRID 1526114 reaction equation
[NH2:1][NH2:2].[C:3]([C:5]1[C:10](=S)[NH:9][C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N+:31]([O-:33])=[O:32])#[N:4]>C(O)C>[NH2:4][C:3]1[C:5]2[C:10](=[N:9][C:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[C:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:6]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])[NH:2][N:1]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 70874350HCID 70874350, compound

Product 1

HCID 178468518HCID 178468518, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 ml of hydrazine is added to a solution of 0.21 g (0.46 mmol) of ethyl 5-cyano-2-(4-methoxyphenyl)-4-(2-nitrophenyl)-6-thioxo-1,6-dihydropyridine-3-carboxylate dissolved in 2 ml of ethanol. The reaction medium is carried at 90° C. for 5 hours. The precipitate obtained is filtered and then recrystallized in a methanol/diethyl ether mixture to yield 0.20 g (74%) of ethyl 3-amino-6-(4-methoxyphenyl)-4-(2-nitrophenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylate in the form of a yellow solid.

Workup

  1. customThe precipitate obtained
  2. filtrationis filtered
  3. customrecrystallized in a methanol/diethyl ether mixture

Sources & evidence

ORD record
ord-d5b6848c9d394a299f649d1213c0b64a
Source dataset
uspto-grants-2015_07
Patent number
US09085575B2

Reaction notes

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