Potassium Hydroxide → 5-Bromo-7-methyl-1H-indole

HRID 1353613ノート

反応式

HRID 1353613 の反応式
C(OC([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Br:15])=[CH:10][C:9]=2[CH3:16])=O)C.[OH-].[K+]>O.C(O)C>[Br:15][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]([CH3:16])[CH:10]=1)[NH:7][CH:6]=[CH:14]2

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 4715166HCID 4715166、化合物

生成物 1

HCID 211022005-Bromo-7-methyl-1H-indole

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

5-Bromo-7-methyl-1H-indole-2-carboxylic acid ethyl ester (5.3 g, 18.7 mmol) was added to a potassium hydroxide solution in 1:1 water/ethanol mixture (20 mL) and heated at reflux for 12 h. After cooling to room temperature, the solvents were removed in vacuo and the resultant residue transferred to a 6N hydrochloric acid solution (20 mL). The white precipitate that formed was filtered, washed severally with water, and dried for several hours. The crude solid was dissolved in quinoline (14 mL) and heated at reflux for 4 h. After cooling to room temperature, the crude mixture was poured into a mixture of ice water (100 mL) and concentrated hydrochloric acid (16 mL), extracted with ethyl acetate (2×), brine (2×), dried over sodium sulfate, and concentrated. Attempts to recrystallize the desired product from isopropanol resulted in significant decomposition. The title compound was obtained by flash chromatography on silica get to afford 1.5 g (38%, 2 steps). LC/MS: tR=1.72 min, 210.05 (MH)+.

後処理

  1. temperatureheated
  2. temperatureat reflux for 12 h
  3. customthe solvents were removed in vacuo
  4. customThe white precipitate that formed
  5. filtrationwas filtered
  6. washwashed severally with water
  7. customdried for several hours
  8. dissolutionThe crude solid was dissolved in quinoline (14 mL)
  9. temperatureheated
  10. temperatureat reflux for 4 h
  11. temperatureAfter cooling to room temperature
  12. additionthe crude mixture was poured into a mixture of ice water (100 mL) and concentrated hydrochloric acid (16 mL)
  13. extractionextracted with ethyl acetate (2×), brine (2×)
  14. dry with materialdried over sodium sulfate
  15. concentrationconcentrated
  16. customto recrystallize the desired product from isopropanol
  17. customresulted in significant decomposition

出典と根拠

ORDレコード
ord-6e09f1a6d9aa49d4a76076b0b7e7ee1b
出典データセット
uspto-grants-2007_05
特許番号
US07220862B2

反応ノート

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