Potassium Carbonate → 4-(2-Methoxyethoxy)-2-nitroaniline

HRID 58177

반응식

HRID 58177 반응식
C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[N+:15]([O-:17])=[O:16].Br[CH2:19][CH2:20][O:21][CH3:22]>CN(C=O)C>[CH3:22][O:21][CH2:20][CH2:19][O:14][C:11]1[CH:12]=[CH:13][C:8]([NH2:7])=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 37588824-Amino-3-Nitrophenol

생성물 1

HCID 204787644-(2-Methoxyethoxy)-2-nitroaniline수율 24%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Powdered and dried Potassium carbonate (3.58 g, 0.025 mol) was added to a solution of 4-amino-3-nitrophenol (2 g, 0.012 mol) in DMF (20 mL) at 0° C. under nitrogen atmosphere. To this, 1-bromo-2-methoxyethane (1.34 mL, 0.014 mol) was added dropwise and the resultant reaction mixture was refluxed for overnight. Then, the reaction mixture was filtered through celite. The filterate was concentrated and diluted with ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (3×30 mL). The organic phase was washed with brine, dried on Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica gel column chromatography to obtain the title compound (0.6 g, yield: 24%) as a solid. MS (ESI): 213.15 [M+H]+.

후처리

  1. customthe resultant reaction mixture
  2. temperaturewas refluxed for overnight
  3. filtrationThen, the reaction mixture was filtered through celite
  4. concentrationThe filterate was concentrated
  5. additiondiluted with ethyl acetate and water
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate (3×30 mL)
  8. washThe organic phase was washed with brine
  9. customdried on Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1f33108501d24d06b7d7c323b2c85e60
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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