ethyl 2-(5-nitro-1H-indol-2-yl)propanoate → ethyl 2-(5-amino-1H-indol-2-yl)propanoate

HRID 1404006ノート

反応式

HRID 1404006 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2)([O-])=O.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)C.C(OCC)(=O)C.O.C([O-])(O)=O.[Na+]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

参加物

7

反応物 2

HCID 59129193ethyl 2-(5-nitro-1H-indol-2-yl)propanoateHCID 85782573Tin tetrachloride dihydrate

生成物 1

HCID 59129453ethyl 2-(5-amino-1H-indol-2-yl)propanoate収率 99.7%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
120 °C

実験手順

To a solution of ethyl 2-(5-nitro-1H-indol-2-yl)propanoate (0.10 g, 0.38 mmol) in ethanol (4 mL) was added tin chloride dihydrate (0.431 g, 1.91 mmol). The mixture was heated in the microwave at 120° C. for 1 h. The mixture was diluted with ethyl acetate before water and saturated aqueous NaHCO3 were added. The reaction mixture was filtered through a plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure to give ethyl 2-(5-amino-1H-indol-2-yl)propanoate (0.088 g, 99%).

後処理

  1. additionwere added
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. customThe organic layer was separated from the aqueous layer
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-2f9210d4c1cd4a58bdcc8ff2281f59ab
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

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