Vanillin → HCID 178492214, compound

HRID 2202621Notes

Reaction equation

HRID 2202621 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:3]=1[C:14]#[N:15].O=[CH:17][C:18]1[CH:26]=[CH:25][C:23]([OH:24])=[C:20]([O:21][CH3:22])[CH:19]=1>CCO.N1CCCCC1>[OH:24][C:23]1[CH:25]=[CH:26][C:18]([CH:17]=[N:1][C:2]2[NH:6][N:5]=[C:4]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:3]=2[C:14]#[N:15])=[CH:19][C:20]=1[O:21][CH3:22]

Participants

5

Reactant 2

HCID 1183VanillinHCID 4164367HCID 4164367, compound

Product 1

HCID 178492214HCID 178492214, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

5-amino-3-(phenylamino)-1H-pyrazole-4-carbonitrile (100 mg) was suspended in EtOH (4 mL) and Vanillin (1 eq.) and piperidine (1 drop) were added. Stirred at reflux until intermediate was absent (HPLC). After reaction was complete (18 hrs) it was brought to room temperature and filtered to obtain A21 as a yellow powder. Powder was washed with EtOH. Product was allowed to dry under vacuum for 1 hr (65 mg, 38.8% yield).

Workup

  1. temperatureat reflux until intermediate
  2. customAfter reaction
  3. custom(18 hrs) it
  4. customwas brought to room temperature
  5. filtrationfiltered
  6. customto obtain A21 as a yellow powder
  7. washPowder was washed with EtOH
  8. customto dry under vacuum for 1 hr (65 mg, 38.8% yield)

Sources & evidence

ORD record
ord-0495e1c8b3ef4b5da69a8b0af13c22e8
Source dataset
uspto-grants-2016_06
Patent number
US09365556B2

Reaction notes

Loading…