Ammonia → 2-Anthracen-9-yl-ethylamine

HRID 910711

反応式

HRID 910711 の反応式
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][C:16]#[N:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[NH4+].[OH-].N>C(O)C.[Ni]>[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[CH2:15][CH2:16][NH2:17])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

参加物

6

反応物 3

HCID 222AmmoniaHCID 14923Ammonium HydroxideHCID 3156629-Anthraceneacetonitrile

生成物 1

HCID 543274372-Anthracen-9-yl-ethylamine収率 85%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

To a solution of anthracen-9-yl-acetonitrile (3.0 g, 13.82 mmol) in ethanol (150 mL) was added concentrated NH4OH (15 mL) and Raney nickel (15 g), and ammonia gas was bubbled through the mixture at 0° C. for 10 minutes. The suspension was hydrogenated for 48 hours at room temperature. Air was bubbled through the solution and Raney nickel was removed by filtration. The filtrate was concentrated and the oily residue was dissolved in CH2Cl2, washed with an aqueous solution of sodium carbonate (Na2CO3, 10%), dried over MgSO4 and concentrated. The resulting solid was purified by recrystallization from a mixture of hexane and CH2Cl2 (7:3) to give 2-anthracen-9-yl-ethylamine as yellow crystals (2.60 g, 85%). 1H NMR (CDCl3) δ 8.37 (1H, s), 8.33 (2H, d), 8.02 (2H, d), 7.54-7.47 (4H, m), 3.86 (2H, t), 3.19 (2H, t), 1.34 (2H, br-s).

後処理

  1. customwas bubbled through the mixture at 0° C. for 10 minutes
  2. customAir was bubbled through the solution and Raney nickel
  3. customwas removed by filtration
  4. concentrationThe filtrate was concentrated
  5. dissolutionthe oily residue was dissolved in CH2Cl2
  6. washwashed with an aqueous solution of sodium carbonate (Na2CO3, 10%)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe resulting solid was purified by recrystallization from a mixture of hexane and CH2Cl2 (7:3)

出典と根拠

ORDレコード
ord-181fe1c4deff4b2caefc14831f34ef0e
出典データセット
uspto-grants-2011_09
特許番号
US08022214B2

関連ノート

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