alpha-Hydrazino-m-cresol dihydrochloride → 6-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-hydroxybenzyl)-4,5-dihydropyridazin-3(2H)-one

HRID 2061415ノート

反応式

HRID 2061415 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:10](=O)[CH2:11][CH2:12][C:13]([OH:15])=O)[CH:5]=[C:6]([Br:9])[C:7]=1[OH:8].Cl.Cl.[OH:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[CH2:23][NH:24][NH2:25]>C(O)C>[Br:9][C:6]1[CH:5]=[C:4]([C:10]2[CH2:11][CH2:12][C:13](=[O:15])[N:24]([CH2:23][C:22]3[CH:26]=[CH:27][CH:28]=[C:20]([OH:19])[CH:21]=3)[N:25]=2)[CH:3]=[C:2]([Br:1])[C:7]=1[OH:8]

参加物

4

反応物 2

HCID 2724402alpha-Hydrazino-m-cresol dihydrochlorideHCID 45806384-(3,5-Dibromo-4-hydroxyphenyl)-4-oxobutanoic acid

生成物 1

HCID 1361599086-(3,5-Dibromo-4-hydroxyphenyl)-2-(3-hydroxybenzyl)-4,5-dihydropyridazin-3(2H)-one収率 49.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A stirred mixture of 4-(3,5-dibromo-4-hydroxyphenyl)-4-oxobutanoic acid (H) (150 mg, 0.426 mmol) and 3-hydroxybenzylhydrazine dihydrochloride (135 mg, 0.639 mmol) in ethanol was heated to reflux. After heating for 16 h, the reaction mixture was cooled down and the precipitate formed was collected and dried in vacuo. This gave the title compound as a red solid (95 mg, 49%)1H NMR δ (ppm) (DMSO-d6): 2.59 (2 H, t), 3.01 (2 H, t, J=8.2 Hz), 4.88 (2H, s), 6.67 (1 H, d, J=8.2 Hz), 6.69-6.76 (2 H, m), 7.14 (1 H, t, J=7.8 Hz), 7.92 (2 H, s), 9.39 (1 H, s), 10.44 (1 H, s). LCMS (10 cm_apci_formic) Rt 3.33 min; m/z 453/455/457 [M+H].

後処理

  1. temperaturewas heated to reflux
  2. temperatureAfter heating for 16 h
  3. temperaturethe reaction mixture was cooled down
  4. customthe precipitate formed
  5. customwas collected
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-4df88f1c7e604e81a5f35556b16e5c94
出典データセット
uspto-grants-2012_10
特許番号
US08283351B2

反応ノート

読み込み中…