Hydrochloric Acid → 4-methoxy-2,3-dihydro-1H-indole

HRID 430779ノート

反応式

HRID 430779 の反応式
[B-][N+](C)(C)C.Cl.[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2>O1CCOCC1>[CH3:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][NH:13]2

参加物

5

反応物 3

HCID 313Hydrochloric Acid2 回HCID 1383634-Methoxy-1H-indoleHCID 6327651Borane,N-dimethylmethanamine (1:1)

生成物 1

HCID 162444414-methoxy-2,3-dihydro-1H-indole収率 83%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Borane-trimethylamine complex (3.00 g) and 10.5N hydrochloric acid (2.25 ml) were added to 4-methoxyindole (1.29 g) in dioxane (20 ml), and the mixture was heated to reflux for 30 minutes. To this mixture, 6N hydrochloric acid (7.00 ml) was added and the mixture was heated to reflux for 15 minutes. The solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution was added to change the aqueous layer to alkaline condition, followed by extracting the aqueous layer with ether (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (1.08 g, yield: 83%).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 15 minutes
  5. customThe solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution
  6. additionwas added
  7. extractionby extracting the aqueous layer with ether (3×20 ml)
  8. washThe obtained organic layers were washed with saturated brine
  9. dry with materialdried over sodium sulfate
  10. customAfter removing solids
  11. filtrationby filtration
  12. customthe solvent was removed under reduced pressure
  13. customthe obtained crude product
  14. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-cc3004f1dd034e4c8e56fa2c8decc2a1
出典データセット
uspto-grants-2001_11
特許番号
US06323235B1

反応ノート

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