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

HRID 58177

反応式

HRID 58177 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 204787644-(2-Methoxyethoxy)-2-nitroaniline収率 24%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-1f33108501d24d06b7d7c323b2c85e60
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

関連ノート

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