Nitric Acid → 1-[1-(4-fluorobenzyl)-4-nitro-1H-pyrrol-2-yl]ethanone

HRID 381503

反応式

HRID 381503 の反応式
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12](=[O:14])[CH3:13])=[CH:4][CH:3]=1.[N+:17]([O-])([OH:19])=[O:18]>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([N+:17]([O-:19])=[O:18])[CH:9]=[C:8]2[C:12](=[O:14])[CH3:13])=[CH:15][CH:16]=1

参加物

4

反応物 2

HCID 944Nitric AcidHCID 4926932-Acetyl-1-(4-fluorobenzyl)pyrrole

生成物 1

HCID 183634661-[1-(4-fluorobenzyl)-4-nitro-1H-pyrrol-2-yl]ethanone

試薬・触媒・溶媒 1

HCID 7918Acetic Anhydride溶媒

反応条件

温度
-78 °C

実験手順

To a 500 mL round bottomed flask with a stirring bar and a drying tube was added 1-[1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone AI-1-1 (11.64 g, 53.58 mmol) and acetic anhydride (230 mL). This solution was cooled to −78° C. and concentrated nitric acid (3.7 mL of 15.9 N solution, 58.24 mmol) was added with a pipette. The cooling bath was allowed to expire and the mixture warmed to 0° C. over 7 h. The acetic anhydride was removed in vacuo and the residue was taken up in EtOAc (500 mL). This solution was washed with saturated aqueous NaHCO3 solution (2×) and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave a solid. This material was chromatographed on silica gel using 20% EtOAc in hexane as eluant. An impure yellow crystalline solid was obtained. This material was recrystallized from Et2O/hexane to give white crystals of 1-[1-(4-fluorobenzyl)-4-nitro-1H-pyrrol-2-yl]ethanone AVI-1-1. 1H NMR (CDCl3) δ 2.55 (3H, s), 5.54 (2H, s), 7.06 (2H, m), 7.20 (2H, m), 7.47 (1H, d, j=1.8 Hz), 7.63 (1H, d, j=1.8 Hz).

後処理

  1. temperaturethe mixture warmed to 0° C. over 7 h
  2. customThe acetic anhydride was removed in vacuo
  3. washThis solution was washed with saturated aqueous NaHCO3 solution (2×) and brine
  4. customDrying
  5. filtration(MgSO4), filtration and removal of the solvent in vacuo
  6. customgave a solid
  7. customThis material was chromatographed on silica gel using 20% EtOAc in hexane as eluant
  8. customAn impure yellow crystalline solid was obtained
  9. customThis material was recrystallized from Et2O/hexane

出典と根拠

ORDレコード
ord-02e55bf0cd3941beae612d0cdb874d8c
出典データセット
uspto-grants-2001_10
特許番号
US06306891B1

関連ノート

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