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

HRID 2236937Notes

Reaction equation

HRID 2236937 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 (2.4 g, 10 mmol) in 25 mL of a 4:1 mixture of acetic anhydride and N,N-dimethylformamide, respectively, is added trimethylorthoformate (2.2 mL, 20 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 to yield 2.4 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

Sources & evidence

ORD record
ord-e926d1b73a28498188dee89c66b834a6
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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