4-Hydroxybenzaldehyde → HCID 178513721, compound

HRID 1049177Notes

Reaction equation

HRID 1049177 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]([NH2:17])=[O:16].[OH:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.N1CCCCC1>C(O)C>[Cl:14][C:10]1[CH:9]=[C:8]([NH:7][C:4]2[C:3]([C:15]([NH2:17])=[O:16])=[C:2]([N:1]=[CH:23][C:22]3[CH:25]=[CH:26][C:19]([OH:18])=[CH:20][CH:21]=3)[NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 8082PiperidineHCID 866989565-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide

Product 1

HCID 178513721HCID 178513721, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-amino-3-((3-chlorophenyl)amino)-1H-pyrazole-4-carboxamide (4.40 g) was suspended in 125.00 mL of ethanol and 4-hydroxybenzaldehyde (4.273, 1.5 eq.) and piperidine (0.50 eq, 865 μL) 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 3-((3-chlorophenyl)amino)-5-((4-hydroxybenzylidene)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 (4.00 g, 65% 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-e8c5d61efefc48829c9d2aebb245ceec
Source dataset
uspto-grants-2016_07
Patent number
US09382237B2

Reaction notes

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