Water → HCID 12277508, compound

HRID 1891038Notes

Reaction equation

HRID 1891038 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[CH:9][CH:10]=[CH:11][CH:12]=[C:5]2[CH2:4][C:3]1=[O:13].Br[CH2:15][CH2:16]Br.C([O-])([O-])=O.[K+].[K+].O>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.CN(C)C=O>[CH3:1][N:2]1[C:3](=[O:13])[C:4]2([CH2:16][CH2:15]2)[C:5]2[C:6](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 3494362-Methylisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 12277508HCID 12277508, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of N-methylhomophthalimide (4.05 kg), 1,2-dibromoethane (2.39 L), and Bu4NHSO4 (785 g) in N,N-dimethylformamide (32 L) were added K2CO3 (6.39 kg) and N,N-dimethylformamide (8.5 L) at room temperature. Then the solution was heated to 70° C., and was stirred for 2 hours at 68˜70° C. After cooling the reaction mixture to 40° C., water (81 L) was added. After the slurry was stirred for 1 hour at 40° C., it was allowed to cool to room temperature and was stirred overnight. The suspension was filtered, and the obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L), twice, and water (20 L), sequentially. It was dried at room temperature under N2 flow for several hours and then under the reduced pressure overnight to afford the title compound as pale pink crystal (4.67 kg, 4.30 kg assay, 92% yield).

Workup

  1. temperatureAfter cooling the reaction mixture to 40° C.
  2. stirringAfter the slurry was stirred for 1 hour at 40° C.
  3. temperatureto cool to room temperature
  4. stirringwas stirred overnight
  5. filtrationThe suspension was filtered
  6. washthe obtained wet crystal was washed with the mixture of N,N-dimethylformamide and water (N,N-dimethylformamide:water=1:1, 20 L)
  7. customIt was dried at room temperature under N2 flow for several hours

Sources & evidence

ORD record
ord-7a0c645d69034a378ae9cc0eba811ae2
Source dataset
uspto-grants-2013_08
Patent number
US08507504B2

Reaction notes

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