4-Hydroxybenzaldehyde → HCID 178513738, compound

HRID 1049162Notes

Reaction equation

HRID 1049162 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[C:3]=1[C:17]([NH2:19])=[O:18].[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1.N1CCCCC1>C(O)C>[OH:20][C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[N:1][C:2]2[NH:6][N:5]=[C:4]([NH:7][C:8]3[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=3)[C:3]=2[C:17]([NH2:19])=[O:18])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 866989655-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513738HCID 178513738, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide was then suspended in 100 mL of ethanol and 4-hydroxybenzaldehyde (12.945 g, 2.00 eq.) and piperidine (0.25 eq.) was added. Stirred the reaction at reflux until starting material was absent and confirmed by HPLC. After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain 5-((4-hydroxybenzylidene)amino)-3-((4-nitrophenyl)amino)-1H-pyrazole-4-carboxamide as a yellow to orange powder. The product was washed with ethanol to remove any excess 4-hydroxybenzaldehyde. Product was allowed to dry under vacuum for 1 hr (9.00 g, 47% yield).

Workup

  1. customthe reaction
  2. temperatureat reflux
  3. customAfter reaction
  4. custom(18 hrs) it
  5. customwas brought to room temperature
  6. filtrationfiltered

Sources & evidence

ORD record
ord-50dcfb7c278840808a2f591a354a2b48
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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