Hydrochloric Acid → Ethyl 3-(4-chlorophenyl)-1h-indole-2-carboxylate

HRID 430646노트

반응식

HRID 430646 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[C:16]1([NH:22]N)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)C.Cl>S(=O)(=O)(O)O.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:22][C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7516PhenylhydrazineHCID 2736395Ethyl 3-(4-chlorophenyl)-2-oxopropanoate

생성물 1

HCID 18351540Ethyl 3-(4-chlorophenyl)-1h-indole-2-carboxylate수율 12%

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 962Water용매

반응 조건

온도
120 °C

실험 절차

A mixture of Example 52A (4.75 g, 21.0 mmol) and phenyl hydrazine (2.07 mL, 21.0 mmol) was treated with concentrated sulfuric acid (5 drops), heated to 120° C. for 15 minutes, cooled to room temperature, treated with ethanol (25 mL), treated with bubbling HCl gas for 2 minutes, and heated to reflux for 1 hour. The mixture was poured into water (30 mL) and extracted with diethyl ether. The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was recrystallized from ethanol to provide 750 mg (12%) 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 (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-bd2de23d808e4c7480e4110de6afcda0
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323228B1

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