Dimethylformamide → 2-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

HRID 1579009Notes

Reaction equation

HRID 1579009 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([NH:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.CN(C)C=O.[OH-].[K+].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27]Br>CO>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][N:13]1[C:14](=[O:15])[C:7]2[CH:6]=[CH:5][CH:4]=[C:3]3[C:8]=2[C:9](=[CH:10][CH:1]=[CH:2]3)[C:11]1=[O:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 80561,4-DibromobutaneHCID 14797Potassium HydroxideHCID 66491Naphthalimide

Product 1

HCID 27823602-(4-bromobutyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 G. (0.5 mole) of 1,8-naphthalimide is suspended in 2100 ml. of dimethylformamide and the mixtrue is heated to 90° to form a complete solution. A solution of 36.3 g. (0.55 mole) of potassium hydroxide (85%) in 100 ml. of methanol is added resulting in the immediate formation of a yellow precipitate. The resulting mixture is stirred for one hour at 90° and cooled to 25°. 245 g. (1.0 mole) of 1,4-dibromobutane is added and the mixture is again heated to 90° and stirred for an additional hour. A precipitate remains in the mixture but is more granular than the initial material. The reaction mixture is cooled and the precipitate filtered off and discarded. The solvent is removed from the filtrate under vacuum and the residue is diluted with 500 ml. of hexane immediately precipitating crude 2-(4-bromobutyl)-1H-benz[de]isoquinoline-1,3(2H)-dione. The precipitate is filtered off, washed with fresh hexane and dried for 2 hours at 50° (0.1 mm.) to yield 2-(4-bromobutyl)-1H-benz[de]isoquinoline-1,3(2H)-dione. An analytically pure sample is prepared by dissolving the above product in hot 95% ethanol and recrystallizing by allowing the solution to cool to 25°. The resulting precipitate is dried for 2 hours at 50° (0.1 mm.) to yield pure 2-(4-bromobutyl)-1H-benz[de]isoquinoline-1,3(2H)-dione, m.p. 113°-115°.

Workup

  1. customto form a complete solution
  2. customresulting in the immediate formation of a yellow precipitate
  3. temperaturecooled to 25°
  4. temperaturethe mixture is again heated to 90°
  5. stirringstirred for an additional hour
  6. temperatureThe reaction mixture is cooled
  7. filtrationthe precipitate filtered off
  8. customThe solvent is removed from the filtrate under vacuum
  9. additionthe residue is diluted with 500 ml
  10. customof hexane immediately precipitating crude 2-(4-bromobutyl)-1H-benz[de]isoquinoline-1,3(2H)-dione
  11. filtrationThe precipitate is filtered off
  12. washwashed with fresh hexane
  13. customdried for 2 hours at 50° (0.1 mm.)

Sources & evidence

ORD record
ord-583d4a8b34be4f0a9fedacb7a1ad85ad
Source dataset
uspto-grants-1976_02
Patent number
US03940398

Reaction notes

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