Triethylamine → 1H-Indole-7-carbonitrile

HRID 1512723ノート

反応式

HRID 1512723 の反応式
[I-].ClC1C=CC=C[N+]=1C.[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:19]=[N:20]O)[CH:12]=[CH:11]1.C(N(CC)CC)C>C1COCC1>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[C:19]#[N:20])[CH:12]=[CH:11]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 734136671H-indole-7-carbaldehyde oxime

生成物 1

HCID 108988161H-Indole-7-carbonitrile収率 97.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

2-chloro-1-methylpyridinium iodide (1.930 g) was added to a solution of 1H-indole-7-carbaldehyde oxime (D1) (1.1 g) in dry THF (80 mL) at RT. After stirring for 10 min, triethylamine (3.35 mL) was added dropwise to the reaction mixture. The reaction mixture was stirred at RT for 2 hours, then was heated to 50° C. and stirred at 50° C. for 2.5 hours. The solvent was evaporated. The residue was dissolved in EtOAc (100 mL) and water (100 mL) was added. The organic fraction was separated, washed with aqueous HCl (0.5 M, 50 mL). The organic fraction was dried over anhydrous magnesium sulfate. The dried solution was concentrated to afford 1H-indole-7-carbonitrile (D2) as a white solid (0.95 g). δH (DMSO-d6, 400 MHz): 6.64 (1H, m), 7.16 (1H, t), 7.56 (1H, m), 7.68 (1H, d), 7.93 (1H, d), 12.02 (1H, br s). MS (ES): C9H6N2 requires 142; found 141.0 (M−H+).

後処理

  1. stirringThe reaction mixture was stirred at RT for 2 hours
  2. stirringstirred at 50° C. for 2.5 hours
  3. customThe solvent was evaporated
  4. dissolutionThe residue was dissolved in EtOAc (100 mL)
  5. additionwater (100 mL) was added
  6. customThe organic fraction was separated
  7. washwashed with aqueous HCl (0.5 M, 50 mL)
  8. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  9. concentrationThe dried solution was concentrated

出典と根拠

ORDレコード
ord-cde488f9bc7c45b685e30f21a3f4d966
出典データセット
uspto-grants-2012_07
特許番号
US08217028B2

反応ノート

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