6-bromo-2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dione → 2-Hydroxy-6-methylthio-benzo[de]isoquinoline-1,3-dione

HRID 278995

Reaction equation

HRID 278995 reaction equation
[CH3:1][S-:2].[Na+].Br[C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:20])[N:10]([OH:19])[C:11](=[O:18])[C:12]3[C:17]=2[C:16]=1[CH:15]=[CH:14][CH:13]=3>C(O)C>[OH:19][N:10]1[C:9](=[O:20])[C:8]2[CH:7]=[CH:6][C:5]([S:2][CH3:1])=[C:16]3[C:17]=2[C:12](=[CH:13][CH:14]=[CH:15]3)[C:11]1=[O:18]

Participants

4

Reactant 2

HCID 7084296-bromo-2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dioneHCID 4378561Sodium methanethiolate

Product 1

HCID 226239682-Hydroxy-6-methylthio-benzo[de]isoquinoline-1,3-dioneYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium thiomethoxide (0.9 g, 12.0 mmol) was added to a solution of 6-bromo-2-hydroxy-benzo[de]isoquinoline-1,3-dione (1.2 g, 4.0 mmol, from Example 4) in ethanol (200 mL). The mixture was refluxed for 48 hours and concentrated. The solid residue was dissolved in water and acidified with concentrated HCl to pH 4. The resulting precipitate was filtered, washed with water, and dried to give 0.8 g of the title compound, mp 301-306° C.;

Workup

  1. temperatureThe mixture was refluxed for 48 hours
  2. concentrationconcentrated
  3. dissolutionThe solid residue was dissolved in water
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4df3298e4d4c4df68b6467bc6320d704
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Linked notes

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