醋酸 → ethyl (2E)-3-[2-(4-cyanopyridin-2-yl)hydrazinyl]prop-2-enoate

HRID 514380

反应方程式

HRID 514380 反应方程式
[NH:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][N:10]=1)[C:6]#[N:7])[NH2:2].CN(C)/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16].CC(O)=O>CCO>[C:6]([C:5]1[CH:8]=[CH:9][N:10]=[C:3]([NH:1][NH:2]/[CH:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:4]=1)#[N:7]

参与物

5

反应物 3

HCID 176醋酸HCID 5369162N,N-二甲氨基丙烯酸乙酯HCID 201187142-Hydrazinylpyridine-4-carbonitrile

产物 1

HCID 86725509ethyl (2E)-3-[2-(4-cyanopyridin-2-yl)hydrazinyl]prop-2-enoate收率 35%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

To a solution of 2-hydrazinylisonicotinonitrile (500 mg, 3.73 mmol, PREPARATION 2) and ethyl (2E)-3-(dimethylamino)prop-2-enoate (534 mg, 3.73 mmol) in 20 mL EtOH was added 4 mL AcOH, before the mixture was heated under reflux conditions overnight. The reaction mixture was cooled and concentrated to dryness. The residue was adjusted to pH >8 with sat'd. aq. NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to dryness. The residue was purified by flash column chromatography (PE/EtOAc=5/1) to give the title compound (300 mg, 35%) as a yellow solid. [M+H] Calc'd for C11H12N4O2, 233. Found, 233.

后处理

  1. temperaturebefore the mixture was heated under reflux conditions overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated to dryness
  4. extractionaq. NaHCO3 and extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by flash column chromatography (PE/EtOAc=5/1)

来源与证据

ORD记录
ord-5ae4f848546b484db7b7cbcbf35a0f68
来源数据集
uspto-grants-2015_08
专利号
US09107916B2

关联笔记

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