Triethylamine → 2-(6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

HRID 575518

反応式

HRID 575518 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=O)[C:5](=[O:14])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[C:18](Cl)(=[O:22])[C:19](Cl)=O.C(N(CC)CC)C.[C:31]1(=O)[CH2:36][CH2:35]CC[C:32]1=[O:37]>ClCCl.CN(C)C=O.CC(C)(O)C#N>[CH3:1][C:2]1[CH:3]=[C:4]([C:15]([CH:19]2[C:18](=[O:22])[CH2:35][CH2:36][CH2:31][C:32]2=[O:37])=[O:17])[C:5](=[O:14])[N:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1

参加物

8

反応物 4

HCID 8471Triethylamine3 回HCID 130061,2-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 127783026-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid

生成物 1

HCID 867092642-(6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6406Acetone Cyanohydrin触媒HCID 6344Dichloromethane溶媒2 回

実験手順

6-Methyl-3-oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid (0.56 g, 2.42 mmol) was stirred in anhydrous dichloromethane (13 ml) and 1 drop of anhydrous dimethylformamide was added. Oxalyl chloride (0.25 mL, 2.90 mmol) was added dropwise to the yellow solution. After 1.5 h the reaction was concentrated in vacuo. The residue obtained was dissolved in dichloromethane (20 ml). To the brown solution anhydrous triethylamine (1 ml), then cyclohexanedione (0.33 g, 2.90 mmol) was added, producing a reddish solution. A further 0.33 ml of anhydrous triethylamine was added. The reaction mixture was stirred at room temperature for 2 h (reaction monitored by LCMS), then acetone cyanohydrin (1 drop) and anhydrous triethylamine (0.67 ml) was added and the reaction was stirred overnight. LCMS indicated the desired product had been formed. The reaction mixture was concentrated in vacuo. The residue obtained was purified using column chromatography (SiO2, Toluene/Triethylamine/Dioxane/EtOH/Water 100:40:20:20:5 by volume) to afford the title compound as an orange oil (382 mg, 49%). 1H NMR (CDCl3) 2.05 (quin, 2H), 2.41 (m, 3H), 2.47 (br s, 2H), 2.73 (br s, 2H), 7.10 (s, 1H), 7.36 (m, 1H), 7.46 (m, 2H), 7.57 (m, 2H), 16.15 (br s, 1H) ppm.

後処理

  1. concentrationAfter 1.5 h the reaction was concentrated in vacuo
  2. customThe residue obtained
  3. customproducing a reddish solution
  4. custom(reaction monitored by LCMS)
  5. stirringthe reaction was stirred overnight

出典と根拠

ORDレコード
ord-46e8411cee534ac49063dd83c0820ef2
出典データセット
uspto-grants-2015_05
特許番号
US09035049B2

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