6-Nitro-m-toluidine → N-(2-ethoxycarbonylethyl)-5-methyl-2-nitroaniline

HRID 441228ノート

反応式

HRID 441228 の反応式
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].Br[CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:17]([O:16][C:14]([CH2:13][CH2:19][NH:7][C:6]1[CH:8]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])=[O:15])[CH3:18]

参加物

5

反応物 3

HCID 113566-Nitro-m-toluidineHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

生成物 1

HCID 22405071N-(2-ethoxycarbonylethyl)-5-methyl-2-nitroaniline収率 56.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of 5-methyl-2-nitroaniline (3.00 g), ethyl bromopropionate (5.35 g) and potassium carbonate (8.18 g) in N,N-dimethylformamide (20 ml) was stirred at 150° C. for 4 hours and the suspension was cooled to ambient temperature. After being filtered, the filtrate was diluted with ethyl acetate and the solution was washed successively with saturated sodium bicarbonate aqueous solution and brine. Drying over magnesium sulfate, filtering and the removal of solvents afforded a crude product. The crude product was triturated with diethyl ether-n-hexane (1:1) to give N-(2-ethoxycarbonylethyl)-5-methyl-2-nitroaniline (2.83 g) as a yellow prisms.

後処理

  1. temperaturethe suspension was cooled to ambient temperature
  2. filtrationAfter being filtered
  3. additionthe filtrate was diluted with ethyl acetate
  4. washthe solution was washed successively with saturated sodium bicarbonate aqueous solution and brine
  5. dry with materialDrying over magnesium sulfate
  6. filtrationfiltering
  7. customthe removal of solvents
  8. customafforded a crude product
  9. customThe crude product was triturated with diethyl ether-n-hexane (1:1)

出典と根拠

ORDレコード
ord-65cf8ec9703e4909a77a4d82230c864b
出典データセット
uspto-grants-1996_05
特許番号
US05521170

反応ノート

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