Ammonia → 2-Amino-3-fluorobenzonitrile

HRID 1167132ノート

反応式

HRID 1167132 の反応式
F[C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[NH3:11]>C(O)C>[CH3:8][CH2:9][CH2:2][CH:3]([CH3:6])[CH3:4].[NH2:11][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

参加物

5

反応物 2

HCID 222AmmoniaHCID 889352,3-Difluorobenzonitrile

生成物 2

HCID 78922-MethylpentaneHCID 27833922-Amino-3-fluorobenzonitrile収率 50%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
140 °C

実験手順

A mixture of 2,3-difluorobenzonitrile (19.0 g, 137 mmol) and ethanol (200 ml) pre-saturated with ammonia gas was heated at 140° C. in an autoclave for 8 h (terminal pressure 200 psi). The mixture was allowed to cool to ambient temperature and evaporated to dryness. The residue was dissolved in water (400 ml) and extracted with diethyl ether (2×300 ml). The combined organics were washed with water (300 ml) and brine (250 ml), dried over anhydrous magnesium sulfate, filtered and evaporated. Trituration with isohexane (150 ml) afforded 2-amino-3-fluorobenzonitrile (9.8 g, 50%) as an off-white solid: 1H NMR (360 MHz, CDCl3) δ 4.47 (2H, s), 6.65-6.71 (1H, m), 7.14-7.20 (2H, m).

後処理

  1. temperatureto cool to ambient temperature
  2. customevaporated to dryness
  3. dissolutionThe residue was dissolved in water (400 ml)
  4. extractionextracted with diethyl ether (2×300 ml)
  5. washThe combined organics were washed with water (300 ml) and brine (250 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-b249ad91cf174e30bceb6514935efe09
出典データセット
uspto-grants-2003_09
特許番号
US06617326B2

反応ノート

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