Formamidine acetate → 5-Bromo-2-chloro-4-methylaniline

HRID 2189142ノート

反応式

HRID 2189142 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([Cl:11])=[CH:4][C:3]=1[CH3:12].C(O)(=O)C.C(N)=N>[Ni].CO>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([Cl:11])=[C:6]([NH2:8])[CH:7]=1

参加物

5

反応物 2

HCID 160693Formamidine acetateHCID 686162921-Bromo-4-chloro-2-methyl-5-nitrobenzene

生成物 1

HCID 686147015-Bromo-2-chloro-4-methylaniline

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

In an autoclave, a mixture of 253 mmol of 1-bromo-4-chloro-2-methyl-5-nitro-benzene [10289-13-1], 2 g of Raney nickel (60% aqueous) and 1.5 g of formamidine acetate in 102 ml of methanol is stirred under an atmosphere of hydrogen (pressure 12 bars) at 80° C. for 1 hour. The mixture is cooled to room temperature, filtered and evaporated. The residue is partitioned between aqueous saturated sodium bicarbonate-solution and tert-butyl-methyl ether. The aqueous phase is extracted with tert-butyl-methyl ether. The combined organic phases are dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue is partitioned between aqueous saturated sodium bicarbonate-solution and tert-butyl-methyl ether
  5. extractionThe aqueous phase is extracted with tert-butyl-methyl ether
  6. dry with materialThe combined organic phases are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

出典と根拠

ORDレコード
ord-69868a80d91e4c45b105acffa6c78cd7
出典データセット
uspto-grants-2012_12
特許番号
US08324235B2

反応ノート

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