Dimethylamine → Indole, 5-bromo-3-(dimethylamino)methyl-

HRID 330277

反応式

HRID 330277 の反応式
[CH2:1]=O.[CH3:3][NH:4][CH3:5].O.[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[CH:11]2>O1CCOCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:5](=[CH:15][CH:16]=1)[NH:4][CH:3]=[C:11]2[CH2:12][N:13]([CH3:1])[CH3:14]

参加物

6

反応物 4

HCID 674DimethylamineHCID 712FormaldehydeHCID 962WaterHCID 249055-Bromoindole

生成物 1

HCID 13249Indole, 5-bromo-3-(dimethylamino)methyl-収率 98%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
5 °C

実験手順

According to A. Ek, et al., J Am. Chem. Soc., 76, 5579 (1954), to an ice-cooled mixture of dioxane (130 mL) acetic acid (130 mL) , 37% aqueous formaldehyde (9.9 mL, 0.133 mol), 40% aqueous dimethylamine (17.6 mL, 0.140 mol), and H2O (10.6 mL) was added a solution of 5-bromoindole (25.0 g, 0.128 mol) in dioxane (130 mL) over 35 minutes. The internal temperature was maintained at 5° C. during the addition. After 2 hours, the cooling bath was removed and stirring was continued at room temperature overnight. The mixture was diluted with H2O (1600 mL), charcoal and celite were added and the mixture was filtered. 2.5 N NaOH (1000 mL) was added and the resulting precipitate was collected by filtration to yield 98% of product as a white solid.

後処理

  1. customthe cooling bath was removed
  2. waitwas continued at room temperature overnight
  3. additionThe mixture was diluted with H2O (1600 mL), charcoal and celite
  4. additionwere added
  5. filtrationthe mixture was filtered
  6. addition2.5 N NaOH (1000 mL) was added
  7. filtrationthe resulting precipitate was collected by filtration

出典と根拠

ORDレコード
ord-a5947a28d4e94a49948e1b5ae2bf71f0
出典データセット
uspto-grants-1990_01
特許番号
US04895860

関連ノート

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