Acetic Anhydride → HCID 68694284, compound

HRID 2236544Notes

Reaction equation

HRID 2236544 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7](=[O:14])[CH2:6]2.[C:15]([O:18][C:19](=O)C)(=O)C.COC(OC)OC>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][C:7](=[O:14])[C:6]2=[CH:15][O:18][CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 592999416-methoxy-4H-isoquinoline-1,3-dione

Product 1

HCID 68694284HCID 68694284, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-methoxy-4H-isoquinoline-1,3-dione (400 mg, 2.1 mmole), 8 mL of a 4:1 mixture of acetic anhydride and N,N-dimethylformamide and trimethylorthoformate (1.7 mL, 15.5 mmole) is stirred and heated to reflux. After 30 minutes the solvents are removed, the residue treated with hexane-ethyl acetate, the solid collected by filtration, washed with fresh hexane-ethyl acetate and dried to give a yellow solid, 317 mg, (65%), mp 245-7° C., MS (ESI): m/z 234.1 (M+H).

Workup

  1. temperatureheated to reflux
  2. customAfter 30 minutes the solvents are removed
  3. additionthe residue treated with hexane-ethyl acetate
  4. filtrationthe solid collected by filtration
  5. washwashed with fresh hexane-ethyl acetate
  6. customdried
  7. customto give a yellow solid, 317 mg, (65%), mp 245-7° C., MS (ESI)

Sources & evidence

ORD record
ord-d3c6d03e80bf460494143fcbb2957e80
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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