Dimethylformamide → 6-Bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

HRID 906405노트

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HRID 906405 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15]O)[CH:6]=[CH:5]2.[Cl-:19].ClC=[N+](C)C.CN([CH:28]=[O:29])C>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][Cl:19])[CH:6]=[C:5]2[CH:28]=[O:29]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 574398956-Bromo-2-(3-hydroxy-2,2-dimethylpropyl)isoquinolin-1(2H)-one

생성물 1

HCID 866409616-Bromo-2-(3-chloro-2,2-dimethylpropyl)-1-oxo-1,2-dihydroisoquinoline-4-carbaldehyde

시약·촉매·용매 1

HCID 962Water용매

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온도
80 °C

실험 절차

A solution of 6-bromo-2-(3-hydroxy-2,2-dimethylpropyl)isoquinolin-1(2H)-one (Example 2a, 0.92 g) dissolved in DMF (5 ml) was treated with (chloromethylene)dimethylammonium chloride (1.90 g) in a sealed tube. The resulting mixture was stirred at 80° C. for 20 h. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (300 mL). The organic was dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified (SiO2 chromatography, elution with 50% diethyl ether in isohexane) to afford the subtitle compound (0.50 g) as a solid.

후처리

  1. extractionextracted with ethyl acetate (300 mL)
  2. dry with materialThe organic was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customto afford crude product
  6. customThe crude product was purified
  7. wash(SiO2 chromatography, elution with 50% diethyl ether in isohexane)

출처 및 근거

ORD 기록
ord-0fa04a274e3a4e2c9d31b9595b9b4b6a
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012980B2

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