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

HRID 430646ノート

反応式

HRID 430646 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bd2de23d808e4c7480e4110de6afcda0
出典データセット
uspto-grants-2001_11
特許番号
US06323228B1

反応ノート

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