Hydrochloric Acid → HCID 54121458, 화합물

HRID 278443

반응식

HRID 278443 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 54121458HCID 54121458, 화합물수율 68%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-86fd5dc6478247c9beb8be490dc96900
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359138B1

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