Hydrochloric Acid → ethyl 3-phenyl-1H-indole-2-carboxylate

HRID 430642노트

반응식

HRID 430642 반응식
O=[C:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:15]1([NH:21]N)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)C.Cl>S(=O)(=O)(O)O.O>[C:9]1([C:8]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:21][C:2]=2[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7516PhenylhydrazineHCID 12292599Ethyl 2-oxo-3-phenylpropanoate

생성물 1

HCID 2763656ethyl 3-phenyl-1H-indole-2-carboxylate수율 32%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

A mixture of Example 1A (7.81 g, 40.7 mmol) and phenylhydrazine (4.00 mL, 40.7 mmol) was treated with concentrated sulfuric acid (4 drops), heated to 120° C. for 15 minutes, cooled to room temperature, treated with ethanol (50 mL), treated with bubbling HCl gas for 2 minutes, and heated to reflux for 1 hour. The mixture was poured into water (100 mL) and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide 3.43 g (32%) of the desired product.

후처리

  1. temperaturecooled to room temperature
  2. temperatureheated
  3. temperatureto reflux for 1 hour
  4. extractionextracted with diethyl ether
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-613d76dc90294ec19f3248afa1b00928
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323228B1

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