Hydrazine hydrate (1:1) → 5-(3-Pyridyl)-2-pyrazoline

HRID 1024357ノート

反応式

HRID 1024357 の反応式
O.[NH2:2][NH2:3].[N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[CH:11][CH:12]=O)[CH:5]=1>CC(O)(C)C>[N:2]1[NH:3][CH:10]([C:6]2[CH:5]=[N:4][CH:9]=[CH:8][CH:7]=2)[CH2:11][CH:12]=1

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 3094653-(Pyridin-3-yl)acrylaldehyde

生成物 1

HCID 30312845-(3-Pyridyl)-2-pyrazoline

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

Under N2 atmosphere, hydrazine hydrate (3.65 mL, 2 equiv.) was added to a solution of 3-(3-pyridyl)acrolein (5.0 g) in t-BuOH (25 mL). The mixture was refluxed for 3 days, followed by evaporation under reduced pressure. The residue was taken up in DCM and washed with 5% aqueous NaHCO3. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. This gave 5.0 g of a red oil, containing 74% of the anticipated product and 26% of the hydrazone intermediate that failed to undergo ring-closure. This material was used in subsequent steps without further purification. Characteristic pyrazoline signals in 1H NMR (400 MHz, CDCl3): δ 2.63-2.75 (m, 1H), 3.13-3.25 (m, 1H), 4.72-4.82 (m, 1H), 6.85 (br s, 1H).

後処理

  1. temperatureThe mixture was refluxed for 3 days
  2. customfollowed by evaporation under reduced pressure
  3. washwashed with 5% aqueous NaHCO3
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated under reduced pressure
  6. additionThis gave 5.0 g of a red oil, containing 74% of the anticipated product and 26% of the hydrazone intermediate that
  7. customThis material was used in subsequent steps without further purification

出典と根拠

ORDレコード
ord-0f2a94adb56a4f418790e130ac722a9f
出典データセット
uspto-grants-2014_05
特許番号
US08722887B2

反応ノート

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