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

HRID 441228노트

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HRID 441228 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
150 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-65cf8ec9703e4909a77a4d82230c864b
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521170

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