Acetic Anhydride → 4-Methoxymethylene-4H-isoquinoline-1,3-dione

HRID 2236913Notes

Reaction equation

HRID 2236913 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=[O:11])[NH:2]1.[C:13]([O:16][C:17](=O)C)(=O)C.COC(OC)OC>CN(C)C=O>[CH3:13][O:16][CH:17]=[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:12])[NH:2][C:3]1=[O:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 3494351,3(2H,4H)-isoquinolinedione

Product 1

HCID 686923374-Methoxymethylene-4H-isoquinoline-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a suspension of 4H-Isoquinoline-1,3-dione (1.5 g, 9.3 mmol) in 22.5 mL of a 4:1 mixture of acetic anhydride and N,N-dimethylformamide, respectively, is added trimethylorthoformate (2.0 mL, 18.6 mmol). The reaction mixture is shaken in a heating block at 125° C. for 1 hour, at which point a beige precipitate formed, product. Upon cooling to room temperature, more product precipitated out. The precipitate is then filtered off, rinsed with copious amounts of ether, and dried to yield 1.47 g of 4-Methoxymethylene-4H-isoquinoline-1,3-dione.

Workup

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

Sources & evidence

ORD record
ord-c6181e060bc548c38102daae58755358
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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