Water → HCID 14281448, compound

HRID 2231225Notes

Reaction equation

HRID 2231225 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[NH:7][C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[H-].[Na+].[Br:19][CH2:20][CH2:21][CH2:22][CH2:23]Br.O>CN(C)C=O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[N:7]([CH2:23][CH2:22][CH2:21][CH2:20][Br:19])[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3

Participants

6

Reactant 4

HCID 962WaterHCID 17204-Aminonaphthalene-1,8-dicarboximideHCID 80561,4-DibromobutaneHCID 24758Sodium hydride

Product 1

HCID 14281448HCID 14281448, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 10.6 g of 6-amino-1H-benz[de]-isoquinoline-1,3(2H)-dione in 250 ml of dimetnylformamide was stirred as 2.6 g of 50% sodium hydride in mineral oil was added. The initial orange suspension turned deep red in color. After ten minutes, a solution of 27 g of 1,4-dibromobutane in 50 ml of dimethylformamide was added. A slightly exothermic reaction was noted, and a deep red solution resulted. The mixture was then stirred at room temperature for sixteen hours, and drowned into 600 ml of cold water. A tarry brown precipitate was obtained, and on standing, bright yellow crystals developed in the supernatant. These were collected and recrystallized from aqueous alcohol to yield the pure title compound mp 175°-176° C. The brown precipitate required several recrystallizations from aqueous alcohol to afford more of the pure title compound.

Workup

  1. additionwas added
  2. waitAfter ten minutes
  3. customA slightly exothermic reaction
  4. customa deep red solution resulted
  5. customA tarry brown precipitate was obtained
  6. customThese were collected
  7. customrecrystallized from aqueous alcohol

Sources & evidence

ORD record
ord-d4445d5846c54ad0b9e034338fae60ea
Source dataset
uspto-grants-1988_11
Patent number
US04782064

Reaction notes

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