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

HRID 906405ノート

反応式

HRID 906405 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0fa04a274e3a4e2c9d31b9595b9b4b6a
出典データセット
uspto-grants-2011_09
特許番号
US08012980B2

反応ノート

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