Trimethyl orthoformate → 4-Methoxymethylene-4H-isoquinoline-1,3-dione

HRID 2236408Notes

Reaction equation

HRID 2236408 reaction equation
[CH:1]([O:6][CH3:7])(OC)OC.[C:8]1(=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10](=[O:18])[NH:9]1>C(OC(=O)C)(=O)C.CN(C)C=O>[CH3:7][O:6][CH:1]=[C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8](=[O:19])[NH:9][C:10]1=[O:18]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
125 °C

Procedure

Trimethyl orthoformate (5.648 mL, 51.56 mmol) is added to a solution of 4H-Isoquinoline-1,3-dione (4 g, 24.82 mmol) in acetic anhydride (41.6 mL) and N,N-dimethylformamide (10.4 mL). After it is heated at 125° C. for 50 min, it is cooled and filtered to collected 3.698 g (73%) of the title compound as a yellow solid. mp 260-261° C.; MS (ESI) m/z 204.04 (M+1). Found: C, 58.34; H, 3.63; N, 10.21.

Workup

  1. temperatureit is cooled
  2. filtrationfiltered
  3. customto collected 3.698 g (73%) of the title compound as a yellow solid

Sources & evidence

ORD record
ord-4d760945aec9449e8f151cff8b929f14
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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