Potassium Carbonate → alpha-(5-Methoxy-1-indolinyl)-m-tolunitrile

HRID 371503

反応式

HRID 371503 の反応式
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH2:13][CH2:12]2.Br[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=1>CN(C=O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=1)[CH2:13][CH2:12]2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 107019745-methoxy-2,3-dihydro-1H-indole

生成物 1

HCID 13408842alpha-(5-Methoxy-1-indolinyl)-m-tolunitrile収率 98.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

An ice cold slurry of 5.89 g (42.6 mmole) of K2CO3 and 5.3 g (35.5 mmole) of 5-methoxyindoline in 55 ml of DMF was treated dropwise with a solution of 7.28 g (37.3 mmole) of α-bromo-m-tolunitrile in 50 ml of DMF. After stirring for 1 hour at room temperature, the reaction mixture was concentrated under high vacuum. The residue was partitioned between methylene chloride (250 ml) and water (250 ml). The organic layer was separated, washed with 5% NaOH (300 ml), brine (300 ml), dried over Na2SO4 and concentrated under vacuum to yield 9.28 g (98.9% yield) of α-(5-methoxy-1-indolinyl)-m-tolunitrile.

後処理

  1. concentrationthe reaction mixture was concentrated under high vacuum
  2. customThe residue was partitioned between methylene chloride (250 ml) and water (250 ml)
  3. customThe organic layer was separated
  4. washwashed with 5% NaOH (300 ml), brine (300 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-1f53645aecc54c68bff5d29683fa6763
出典データセット
uspto-grants-1985_07
特許番号
US04532333

関連ノート

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