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

HRID 2236632Notes

Reaction equation

HRID 2236632 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-ff2caff21df4443785b1d3e0ee5ad357
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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