Methanol → 2-fluoro-N1-(3-(tetrahydrofuran-2-yl)propyl)benzene-1,4-diamine

HRID 56219ノート

反応式

HRID 56219 の反応式
[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][O:9]1.CO.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>[Fe].O>[F:1][C:2]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][O:9]1

参加物

7

反応物 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 900235572-fluoro-4-nitro-N-(3-(tetrahydrofuran-2-yl)propyl)aniline

生成物 1

HCID 1179660562-fluoro-N1-(3-(tetrahydrofuran-2-yl)propyl)benzene-1,4-diamine収率 61%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-fluoro-4-nitro-N-(3-(tetrahydrofuran-2-yl)propyl)aniline (480 mg, 1.79 mmol), MeOH (40 mL), water (20 mL), iron powder (504 mg, 9.03 mmol) and NH4Cl (193 mg, 3.61 mmol) was stirred at 60° C. overnight. The mixture was then cooled to rt and saturated NaHCO3 aqueous solution was added. The resulting mixture was filtered and the filtrate was extracted with DCM (30 mL×4). The combined organic layers were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as red liquid (260 mg, 61%).

後処理

  1. temperatureThe mixture was then cooled to rt
  2. filtrationThe resulting mixture was filtered
  3. extractionthe filtrate was extracted with DCM (30 mL×4)
  4. washThe combined organic layers were washed with brine (40 mL×3)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

出典と根拠

ORDレコード
ord-53639d55a8134301bc16f923e99fba65
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

反応ノート

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