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

HRID 906405Notes

Reaction equation

HRID 906405 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0fa04a274e3a4e2c9d31b9595b9b4b6a
Source dataset
uspto-grants-2011_09
Patent number
US08012980B2

Reaction notes

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