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

HRID 514380

反応式

HRID 514380 の反応式
[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]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 5369162Ethyl trans-3-dimethylaminoacrylateHCID 201187142-Hydrazinylpyridine-4-carbonitrile

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-5ae4f848546b484db7b7cbcbf35a0f68
出典データセット
uspto-grants-2015_08
特許番号
US09107916B2

関連ノート

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