Methyl 4-hydrazinylbenzoate → Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate

HRID 509719

反応式

HRID 509719 の反応式
[NH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)[NH2:2].Br[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:22])=[N:20][CH:21]=1>C(N(CC)CC)C>[CH3:22][C:19]1[N:20]=[CH:21][C:16]([CH2:15][CH2:14][N:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:11][CH:12]=2)[NH2:2])=[CH:17][CH:18]=1

参加物

4

反応物 2

HCID 408928Methyl 4-hydrazinylbenzoateHCID 533058565-(2-Bromoethyl)-2-methylpyridine

生成物 1

HCID 68735268Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate収率 28.5%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

Methyl 4-hydrazinylbenzoate (1 g, 0.005 moles) and 5-(2-bromoethyl)-2-methylpyridine (1 g, 0.005 moles) was taken up in triethylamine (2.1 mL) and stirred at RT for 1 hr. The reaction was heated at 100° C., overnight. LCMS analysis of the reaction mixtures shows the formation of product. The reaction mixture was concentrated, water (20 mL) was added to the reaction mixture and the mixture extracted with ethyl acetate. The crude product was dissolved in ethyl acetate and purified by column chromatography using neutral alumina, using 100% ethyl acetate as the eluent. After chromatography 400 mg of Methyl 4-(1-(2-(6-methylpyridin-3-yl)ethyl)hydrazinyl)benzoate was obtained, 28.5% yield.

後処理

  1. temperatureThe reaction was heated at 100° C., overnight
  2. customLCMS analysis of the reaction mixtures
  3. concentrationThe reaction mixture was concentrated
  4. additionwater (20 mL) was added to the reaction mixture
  5. extractionthe mixture extracted with ethyl acetate
  6. dissolutionThe crude product was dissolved in ethyl acetate
  7. custompurified by column chromatography

出典と根拠

ORDレコード
ord-c6ac98b775524cb3a8456186163c2323
出典データセット
uspto-grants-2015_08
特許番号
US09096591B2

関連ノート

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