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

HRID 878537

反应方程式

HRID 878537 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-d3073c1027dd41739d74cc49955b4e3d
来源数据集
uspto-grants-2015_03
专利号
US08987461B2

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