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

HRID 128887

반응식

HRID 128887 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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.

출처 및 근거

ORD 기록
ord-e19703a5a74e4b5582c880d49e3aa30e
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466397

연결된 노트

불러오는 중…