Hydrochloric Acid → 5-(3-Hydroxy-4-methoxyphenyl)-3-(3-hydroxy-4-methoxystyryl)-1-(4-nitrophenyl)-4,5-dihydropyrazole

HRID 128887

Reaction equation

HRID 128887 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12](=O)[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([OH:23])[CH:16]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N+:25]([C:28]1[CH:33]=[CH:32][C:31]([NH:34][NH2:35])=[CH:30][CH:29]=1)([O-:27])=[O:26].Cl>C(O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:10]2[N:34]([C:31]3[CH:30]=[CH:29][C:28]([N+:25]([O-:27])=[O:26])=[CH:33][CH:32]=3)[N:35]=[C:12]([CH:13]=[CH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([OH:23])[CH:16]=3)[CH2:11]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3310889(4-Nitrophenyl)hydrazineHCID 544608681,5-Bis(3-hydroxy-4-methoxyphenyl)penta-1,4-dien-3-one

Product 1

HCID 542328925-(3-Hydroxy-4-methoxyphenyl)-3-(3-hydroxy-4-methoxystyryl)-1-(4-nitrophenyl)-4,5-dihydropyrazoleYield 97.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 1,5-bis(3-hydroxy-4-methoxyphenyl)-1,4-pentadien-3-one (29.6 g, 90.8 mmol), absolute ethanol (220 mL), and 4-nitrophenylhydrazine (16.8 g, 100 mmol for 90 percent purity, 10 percent water) was added conc. HCl (20 mL), and the mixture was stirred and heated at reflux for 24 hours. The mixture was then stirred at room temperature for 16 hours, and the orange crystals that formed were removed by filtration. The product was washed with ethanol and hexane, and dried in a vacuum oven at 90°-100° C. for 12 hours. The product was obtained as orange-red microcrystals (37.2 g, 97.4 percent yield) mp 215°-217° C.; 1H NMR (DMSO-d6) δ9.09 (s, 2H), 8.05 (d, 2H, J=9.5 Hz), 7.06-6.61 (m, 10H), 5.52 (dd, 1H, J1=11.6 Hz, J2= 4.1 Hz,), 3.80 (s, 3H), 3.76 (m, 1H), 3.73 (s, 3H), and 3.07 (m, 1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. stirringThe mixture was then stirred at room temperature for 16 hours
  4. customthe orange crystals that formed
  5. customwere removed by filtration
  6. washThe product was washed with ethanol and hexane
  7. customdried in a vacuum oven at 90°-100° C. for 12 hours
  8. customThe product was obtained as orange-red microcrystals (37.2 g, 97.4 percent yield) mp 215°-217° C.

Sources & evidence

ORD record
ord-e19703a5a74e4b5582c880d49e3aa30e
Source dataset
uspto-grants-1995_11
Patent number
US05466397

Linked notes

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