Acetic Anhydride → 4-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

HRID 2236629Notes

Reaction equation

HRID 2236629 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[CH2:5]2.[C:14]([O:17][C:18](=O)C)(=O)C.COC(OC)OC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][C:6](=[O:13])[C:5]2=[CH:14][O:17][CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 120233176-Bromoisoquinoline-1,3-diol

Product 1

HCID 686927644-methoxymethylene-6-bromo-4H-isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a suspension of 6-Bromo-4H-isoquinoline-1,3-dione (1.0 g, 4.15 mmol) in 8.7 mL of a 4:1 mixture of acetic anhydride and N,N-dimethylformamide, respectively, is added trimethylorthoformate (940 μL, 8.6 mmol). The reaction mixture is shaken in a heating block at 125° C. for 1 hour. Upon cooling to room temperature, the product precipitated out. The precipitate is then filtered off, rinsed with copious amounts of ether, and dried under vacuum to yield 1.0 g of 6-Bromo-4-methoxymethylene-4H-isoquinoline-1,3-dione.

Workup

  1. temperatureUpon cooling to room temperature
  2. customthe product precipitated out
  3. filtrationThe precipitate is then filtered off
  4. washrinsed with copious amounts of ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6b0b036f348b4b2ab96525d8b2852b26
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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