三乙胺 → 2-(3-Oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

HRID 58939

反应方程式

HRID 58939 反应方程式
[O:1]=[C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][CH:5]=[N:4][N:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[C:17](Cl)(=[O:21])[C:18](Cl)=O.C(N(CC)CC)C.[C:30]1(=O)[CH2:35][CH2:34]CC[C:31]1=[O:36]>ClCCl.CN(C)C=O.CC(C)(O)C#N>[O:1]=[C:2]1[C:7]([C:8]([CH:18]2[C:17](=[O:21])[CH2:34][CH2:35][CH2:30][C:31]2=[O:36])=[O:10])=[CH:6][CH:5]=[N:4][N:3]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参与物

8

反应物 4

HCID 8471三乙胺3 次HCID 130061,2-环己二酮HCID 65578草酰氯HCID 46380363-Oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid

产物 1

HCID 627050522-(3-Oxo-2-phenyl-2,3-dihydropyridazine-4-carbonyl)-cyclohexane-1,3-dione

试剂、催化剂与溶剂 3

HCID 6228N,N-二甲基甲酰胺催化剂HCID 6406丙酮氰醇催化剂HCID 6344二氯甲烷溶剂2 次

实验过程

3-Oxo-2-phenyl-2,3-dihydropyridazine-4-carboxylic acid (0.52 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 suspension resulting in a brown 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 coloured 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 mixture 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), and then further purified by column chromatography (SiO2, hexane/ethyl acetate/acetic acid 2:1:0.02 to 0:100:2) to afford the title compound as an orange oil (25 mg, 3% yield). 1H NMR (CDCl3) 2.04 (m, 2H), 2.61 (br s, 4H), 7.18 (d, 1H) 7.46 (m, 2H), 7.59 (m, 3H) 7.96 (d, 1H) ppm.

后处理

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

来源与证据

ORD记录
ord-123aabe408c3429d87b98aee957b6dd2
来源数据集
uspto-grants-2016_09
专利号
US09439428B2

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