Dimethylformamide → HCID 178514998, compound

HRID 231548Notes

Reaction equation

HRID 231548 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:9](=[O:10])[C:8]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:7]2[C:6]1=[O:15].[C:16]([O-:19])([O-])=O.[K+].[K+].[CH3:22][N:23]([CH:25]=[O:26])C>O>[C:9]1(=[O:10])[N:5]([CH2:4][CH2:3][CH2:2][O:19][C:16]2[CH:12]=[CH:13][CH:14]=[C:7]3[C:8]=2[CH:9]=[CH:22][N:23]=[C:25]3[OH:26])[C:6](=[O:15])[C:7]2=[CH:14][CH:13]=[CH:12][CH:11]=[C:8]12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21611N-3-Bromopropylphthalimide

Product 1

HCID 178514998HCID 178514998, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-(3-Bromopropyl) phthalimide (164 g) is added to a stirred solution of 5-hydroxy-1,2-dihydro-1-(2H)-isoquinolone (96.7 g) and anhydrous K2CO3 (91.2 g) in 750 ml of DMF. The reaction mixture is stirred at room temperature for one week, diluted with 3 liters of H2O and stirring continued at RT for an additional 30 minutes. The reaction mixture is filtered and the solid resuspended in 2 liters of H2O and stirred at RT for an additional 11/2 hours. The suspension is filtered and the solid dried in air. The dried solid is broken up, suspended in 750 ml of chloroform and stirred vigorously at RT for 1 hour. The suspension is filtered and the solid dried. The crude product (95.8 g) is dissolved in 2.5 liters in boiling glacial acetic acid. The resulting dark solution is concentrated and cooled. The crystalline precipitate is collected and dried, washed with diethyl ether, resuspended in diethyl ether, stirred at RT for 30 minutes, filtered and dried in vacuo overnight, yielding 59.3 g of the desired product, M.P. >300° C.

Workup

  1. stirringstirring
  2. filtrationThe reaction mixture is filtered
  3. stirringstirred at RT for an additional 11/2 hours
  4. filtrationThe suspension is filtered
  5. customthe solid dried in air
  6. stirringstirred vigorously at RT for 1 hour
  7. filtrationThe suspension is filtered
  8. customthe solid dried
  9. dissolutionThe crude product (95.8 g) is dissolved in 2.5 liters
  10. concentrationThe resulting dark solution is concentrated
  11. temperaturecooled
  12. customThe crystalline precipitate is collected
  13. customdried
  14. washwashed with diethyl ether
  15. stirringstirred at RT for 30 minutes
  16. filtrationfiltered
  17. customdried in vacuo overnight

Sources & evidence

ORD record
ord-14ff5d6ee5194790a20e6921f3dc6ba9
Source dataset
uspto-grants-1989_07
Patent number
US04847264

Reaction notes

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