Acetic Anhydride → (4E)-6-bromo-7-methoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

HRID 2236534Notes

Reaction equation

HRID 2236534 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])[CH2:5]2.[C:16]([O:19][C:20](=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][C:11]=1[O:12][CH3:13])[C:8](=[O:14])[NH:7][C:6](=[O:15])/[C:5]/2=[CH:16]/[O:19][CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 593001906-bromo-7-methoxy-4H-isoquinoline-1,3-dione

Product 1

HCID 59300399(4E)-6-bromo-7-methoxy-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-Bromo-7-methoxy-4H-isoquinoline-1,3-dione (275 mg, 1.02 mmole), 7 mL of a 4:1 mixture of acetic anhydride and N,N-dimethylformamide and trimethylorthoformate (0.8 mL, 7.28 mmole) is stirred and heated to reflux. After 30 minutes the solvents are removed and the solid collected with ether. A brown solid, 202 mg, (63%), mp 245-248° C. dec, MS (ESI): m/z 310.1, 312.1 (M−H).

Workup

  1. temperatureheated to reflux
  2. customAfter 30 minutes the solvents are removed
  3. customthe solid collected with ether

Sources & evidence

ORD record
ord-df68371643df43d398d1c45856c1ac73
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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