Hydrochloric Acid → HCID 178489125、化合物

HRID 895358ノート

反応式

HRID 895358 の反応式
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH2:18])=[CH:8][CH:7]=1.[N:19]([O-])=O.[Na+].Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:34]2[CH2:35][C:36](=[O:39])[NH:37][N:38]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].C([O-])(=O)C.[Na+]>O.C(O)C>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH:18][N:19]=[C:35]2[C:34]([C:28]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=3)=[N:38][NH:37][C:36]2=[O:39])=[CH:8][CH:7]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 152835193-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-oneHCID 223532056-(3-Bromo-propoxy)-biphenyl-3-ylamineHCID 23668193Sodium Nitrite

生成物 1

HCID 178489125HCID 178489125、化合物収率 27.2%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒2 回

実験手順

6-(3-Bromo-propoxy)-biphenyl-3-ylamine (r, 250 mg, 0.82 mmol) was diazotized with sodium nitrite (67 mg, 0.98 mmol) in 1:1 water/ethanol and 0.5 mL concentrated HCl at 0° C. After approximately 1 hour, the diazonium solution was added dropwise to a suspension of 5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (200 mg, 0.9 mmol) and sodium acetate (1.1 g) in 10 mL 1:1 water/ethanol. The orange solid which precipitated was filtered and washed with water and dried. The crude product was purified by silica gel chromatography (eluent: 5% methanol/DCM) to afford 120 mg of 4-{[6-(3-bromo-propoxy)-biphenyl-3-yl]-hydrazono}-5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (s): HPLC (Rt) 5.02 min; m/e 536.1, MS (ES+): 538.9; 1H NMR (500 MHz, CDCl3): 13.9 (bs, 1H), 9.0 (bs, 1H), 7.7-6.9 (m, 11H), 4.1 (m, 2H), 3.9 (s, 3H), 3.7 (s, 3H), 3.5 (m, 2H), 3.3 (m, 2H), 2.2 (m, 2H) and 2.1 (m, 2H).

後処理

  1. customThe orange solid which precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customThe crude product was purified by silica gel chromatography (eluent: 5% methanol/DCM)

出典と根拠

ORDレコード
ord-5c42b6987f7948fbaa95e8dc46a0e3d7
出典データセット
uspto-grants-2005_07
特許番号
US06916798B2

反応ノート

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