Hydrochloric Acid → HCID 54121458、化合物

HRID 278443

反応式

HRID 278443 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)=[O:5])C.[Mg].Cl>CO>[CH3:1][O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[NH:7]1)=[O:5]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 5462224Magnesium

生成物 1

HCID 54121458HCID 54121458、化合物収率 68%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

To 5-methoxy-1H-indole-2-carboxylic acid ethyl ester (5 g, 22.8 mmol) in MeOH (150 ml) was added magnesium turnings (2.2 g, 91.6 mmol, 4eq.) and the mixture vigorously mechanically stirred (10-30° C.) for 2 hr. 4N HCl was added (to pH1-2), then 25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml). The combined extracts were then washed with satd. NaCl solution (50 ml), dried (Na2SO4) filtered and evaporated. The crude green oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:3) to afford the title compound (3.21g, 15.5 mmol, 68%) as a yellow solid Mp. 59-61° C., MS: m/e=207.1 (M+).

後処理

  1. extraction25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml)
  2. washThe combined extracts were then washed with satd
  3. dry with materialNaCl solution (50 ml), dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude green oil was chromatographed over SiO2 (Merck 230-400 mesh)
  7. washeluting with EtOAc-nHexane (1:3)

出典と根拠

ORDレコード
ord-86fd5dc6478247c9beb8be490dc96900
出典データセット
uspto-grants-2002_03
特許番号
US06359138B1

関連ノート

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