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

HRID 2236458Notes

Reaction equation

HRID 2236458 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.[CH:14](OC)(OC)[O:15][CH3:16].C(OC(=O)C)(=O)C>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:15][CH3:16]

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-dioneYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

6-Bromo-4H-isoquinoline-1,3-dione (120 mg, 0.500 mmol) and trimethyl orthoformate (106 mg, 1.00 mmol) were suspended in 1.25 ml of a 1:4 ratio mixture of acetic anhydride and N,N-dimethylformamide. Mixture is heated at 125° C. for 2 hours causing a yellow solid to form. Mixture is cooled to room temperature and filtered. Residue is washed with 20 ml of ethyl ether to afford the product as a yellow solid (109 mg, 0.380 mmol, 77%); 1H NMR (DMSO-d6) δ 4.25 (s, 3H), 7.60 (dd, J=1.9, 8.4 Hz, 1H), 7.96 (d, J=8.5 Hz, 1H), 8.07 (s, 1H), 8.36 (d, J=1.9 Hz, 1H), 11.38 (s, 1H); mass spectrum [(+) ESI], m/z 282/284 (M+H)+.

Workup

  1. customto form
  2. temperatureMixture is cooled to room temperature
  3. filtrationfiltered
  4. washResidue is washed with 20 ml of ethyl ether

Sources & evidence

ORD record
ord-5e471bec176e48e995d9dd3a9c43c92c
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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