Hydrazine hydrate (1:1) → 3-Methoxy-4-nitrobenzohydrazide

HRID 419334

反応式

HRID 419334 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6](OC)=[O:7].O.[NH2:17][NH2:18]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([NH:17][NH2:18])=[O:7]

参加物

4

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 287308Methyl 3-methoxy-4-nitrobenzoate

生成物 1

HCID 218838753-Methoxy-4-nitrobenzohydrazide収率 71%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

To methyl 3-methoxy-4-nitrobenzoate (5.16 g, 24.5 mmol) in EtOH (250 mL) was added hydrazine monohydrate (5.95 mL, 122 mmol) in one portion. The reaction was heated at 80° C. overnight and concentrated upon completion by TLC. The residue was taken up in EtOAc, heated and hot filtered. The filtrate was concentrated and the residue was triturated with diethyl ether to provide the title compound (3.65 g, 17.3 mmol, 71%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.96 (s, 3H), 4.60 (br. s., 2H), 7.50 (dd, J=8.4, 1.5 Hz, 1H), 7.69 (d, J=1.8 Hz, 1H), 7.93 (d, J=8.1 Hz, 1H), 10.05 (br. s., 1H).

後処理

  1. concentrationconcentrated upon completion by TLC
  2. temperatureheated
  3. concentrationThe filtrate was concentrated
  4. customthe residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-8caec853cd82465a9d01bdaf8f8adf24
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

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