Nitric Acid → N-(4-Methoxy-3-nitrophenethyl)acetamide

HRID 551599

反応式

HRID 551599 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:5][CH:4]=1.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][NH:11][C:12](=[O:14])[CH3:13])=[CH:7][C:8]=1[N+:15]([O-:17])=[O:16]

参加物

4

反応物 2

HCID 944Nitric AcidHCID 584258N-(2-(4-Methoxyphenyl)ethyl)acetamide

生成物 1

HCID 15491289N-(4-Methoxy-3-nitrophenethyl)acetamide

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
32.5 °C

実験手順

A solution of 70 g of N-[2-(4-methoxyphenyl)ethyl]acetamide in 330 mL of acetic acid was introduced slowly into 350 mL of 70% nitric acid so that the temperature was between 30-35° C. The addition process took 1 hour. The mixture was stirred at 30-35° C. for additional 40 minutes and was then poured into 1500 mL of ice water. The resulting slurry was extracted with chloroform (2×400 mL). The organic phase was extracted with a saturated aqueous solution of NaHCO3 (2×400 mL) and then with water (2×400 mL). The solvent was then removed by rotary evaporation to produce 65 g of N-[2-(4-methoxy-3-nitrophenyl)ethyl]acetamide, which was further purified by recrystallization from ethyl acetate to yield 48 g (55.6% yield) of yellow crystals. 1HNMR (DMSO-d6) spectrum was consistent with the desired product.

後処理

  1. customwas between 30-35° C
  2. extractionThe resulting slurry was extracted with chloroform (2×400 mL)
  3. extractionThe organic phase was extracted with a saturated aqueous solution of NaHCO3 (2×400 mL)
  4. customThe solvent was then removed by rotary evaporation

出典と根拠

ORDレコード
ord-5715b1a7819644afa50b137ec9f43836
出典データセット
uspto-grants-2011_05
特許番号
US07947761B2

関連ノート

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