Ammonium Hydroxide → HCID 118024571、化合物

HRID 58198ノート

反応式

HRID 58198 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:10][CH3:11])[CH3:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH4+:15].[OH-].CCOC(C)=O.O>C1COCC1>[CH3:11][O:10][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([NH2:15])=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)[CH3:9]

参加物

5

反応物 3

HCID 14923Ammonium Hydroxide2 回HCID 179959131-Fluoro-4-(1-methoxyethyl)-2-nitrobenzeneHCID 22728543Water ethylacetate

生成物 1

HCID 118024571HCID 118024571、化合物収率 44.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1-fluoro-4-(1-methoxyethyl)-2-nitrobenzene (664 g, 3.33 mmol) was stirred in THF (10 ml). NH4OH (0.39 ml, 10.0 mmol) was added and the reaction mixture was stirred at room temperature for 2 hours. Further 780 ul of NH4OH was added and the reaction mixture was heated at 120° C. for 10 minutes using microwave (Biotage Initiator) and then at 140° C. for 50 minutes. After cooling to room temperature, the reaction mixture was poured into EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and evaporated. The resulting material was purified by flash chromatography on silica eluting with 0% to 50% EtOAc/Hexane to afford the title compound (290 mg, yield: 44%). 1H-NMR (400 MHz, CDCl3) δ 1.42 (d, 3H) 3.22 (s, 3H) 4.24 (q, 1H) 6.05 (br. s., 2H) 6.83 (d, 1H) 7.38 (dd, 2.01 Hz, 1H) 8.04 (d, 1H)

後処理

  1. temperaturethe reaction mixture was heated at 120° C. for 10 minutes
  2. waitat 140° C. for 50 minutes
  3. temperatureAfter cooling to room temperature
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe resulting material was purified by flash chromatography on silica eluting with 0% to 50% EtOAc/Hexane

出典と根拠

ORDレコード
ord-07a6a495066a456f990f14a7b0f889a0
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

反応ノート

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