Hydrochloric Acid → 4-Hydroxyindole-3-carboxaldehyde

HRID 25332

反応式

HRID 25332 の反応式
P(Cl)(Cl)(Cl)=O.[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[OH-].[Na+].Cl.CN(C)[CH:21]=[O:22]>O>[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9]([CH:21]=[O:22])=[CH:10][NH:11]2

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6228Dimethylformamide2 回HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 754211H-indol-4-ol

生成物 1

HCID 98152824-Hydroxyindole-3-carboxaldehyde収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Phosphorous oxychloride 7.35 ml was added dropwise to dry dimethylformamide 15 ml under cooling in ice-methanol bath and the mixture was stirred for 15 min. Then, a solution of the 4-hydroxyindole 5.0 g in dry dimethylformamide 10 ml was added dropwise to the mixture under cooling in ice and the mixture was stirred for 2 h at room temperature. Water was added under cooling in ice to the mixture, which was made alkaline with a 30% aqueous sodium hydroxide solution and was stirred for 15 min. Then, the mixture was acidified to pH 4 with 5N-HCl and the precipitate was collected by filtration, washed with water and dried to give the titled compound 4.99 g as crude crystalline materials. Yield 82%. Crude crystalline materials are recrystallized from methanol to give yellow crystals m.p. 190-193° C.

後処理

  1. temperatureunder cooling in ice
  2. stirringthe mixture was stirred for 2 h at room temperature
  3. temperatureunder cooling in ice to the mixture, which
  4. stirringwas stirred for 15 min
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-2970d5c5affd4345a64be8337930ba6f
出典データセット
uspto-grants-2005_02
特許番号
US06858640B2

関連ノート

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