N-bromobutanimide → HCID 22624027, compound

HRID 279005Notes

Reaction equation

HRID 279005 reaction equation
[OH:1][N:2]1[C:11](=[O:12])[C:10]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[C:3]1=[O:18].[Br:19]N1C(=O)CCC1=O>C(O)(=O)C>[Br:19][C:14]1[C:15]([O:16][CH3:17])=[C:8]2[CH:7]=[CH:6][CH:5]=[C:4]3[C:9]2=[C:10]([CH:13]=1)[C:11](=[O:12])[N:2]([OH:1])[C:3]3=[O:18]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2210746HCID 2210746, compound

Product 1

HCID 22624027HCID 22624027, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-hydroxy-6-methoxy-benzo[de]isoquinoline-1,3-dione (0.12 g, 0.5 mmol, from Example 17) and N-bromosuccinimide (0.13 g, 0.7 mmol) in acetic acid (20 mL) was sonicated at 60° C. for 24 hours. The mixture was transferred to a preheated oil bath at 100° C. with vigorous stirring for another 24 hours. The precipitate was filtered, washed with water, dried, and recrystallized from methanol to give 0.05 g of the title compound, mp 223-227° C.;

Workup

  1. customwas sonicated at 60° C. for 24 hours
  2. customThe mixture was transferred to a preheated oil bath at 100° C.
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customdried
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-59605528ffab4d3a8c883eb6d5cc36e4
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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