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Phenylhydrazine → N'-phenyl-2-pyridin-4-ylacetohydrazide

HRID 1867612
ノート
印刷プレビュー

反応式

HRID 1867612 の反応式
Cl.CN(C)CCCN=C=NCC.O.N1(O)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[N:16]=[N:15]1.C(N(CC)C(C)C)(C)C.C1(NN)C=CC=CC=1.Cl.[N:42]1[CH:47]=[CH:46][C:45]([CH2:48][C:49](O)=[O:50])=[CH:44][CH:43]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O.ClCCl>[C:17]1([NH:16][NH:15][C:49](=[O:50])[CH2:48][C:45]2[CH:46]=[CH:47][N:42]=[CH:43][CH:44]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 6

HCID 7516PhenylhydrazineHCID 810974-Pyridineacetic acid hydrochlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 68566518
N'-phenyl-2-pyridin-4-ylacetohydrazide
収率 19.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (2.06 g, 10.76 mmol, 2.02 mmol), 1H-1,2,3-benzotriazol-1-ol hydrate (1.45 g, 10.76 mmol), N,N-diisopropylethylamine (4.69 mL, 26.9 mmol), and phenyl hydrazine (970 mg, 8.97 mmol) were added to a solution of 4-pyridylacetic acid hydrochloride (1.23 g, 8.97 mmol) in dimethylformamide (10 mL). After 16 h, the reaction was worked up with dichloromethane and saturated sodium bicarbonate. The organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (99% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (400 mg). MS 228.5 (M+1)

後処理

  1. washThe organic extracts were washed with brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (99% dichloromethane→12% methanol {1% ammonium hydroxide}/dichloromethane)

出典と根拠

ORDレコード
ord-f205cadb48294561bdc0a579afa19181
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07632832B2

反応ノート

読み込み中…

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