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

HRID 544146

반응식

HRID 544146 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b79453d266a24ff591e6fc67bb48d861
출처 데이터셋
uspto-grants-1984_05
특허 번호
US04448784

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