Acetic Anhydride → HCID 68690990, compound

HRID 2236555Notes

Reaction equation

HRID 2236555 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[C:16](=[O:20])[NH:15][C:14](=[O:21])[CH2:13]3)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:22]([O:25][C:26](=O)C)(=O)C.COC(OC)OC>CN(C)C=O>[CH3:22][O:25][CH:26]=[C:13]1[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([O:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:11]=2)[C:16](=[O:20])[NH:15][C:14]1=[O:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 59299880HCID 59299880, compound

Product 1

HCID 68690990HCID 68690990, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(2-morpholin-4-yl-ethoxy)-4H-isoquinoline-1,3-dione (390 mg, 1.34 mmole), 10 mL of a 4:1 mixture of acetic anhydride and N,N-dimethylformamide and trimethylorthoformate (1.1 mL, 10.1 mmole) is stirred and heated to reflux. After 30 minutes the solvents are removed and the residue treated with 2:1 hexanes/ethyl acetate, the product is collected by filtration, a yellow solid, 230 mg, (52%), MS (ES+): m/z 333.2 (M+H), used as is in the next step.

Workup

  1. temperatureheated to reflux
  2. customAfter 30 minutes the solvents are removed
  3. additionthe residue treated with 2:1 hexanes/ethyl acetate
  4. filtrationthe product is collected by filtration

Sources & evidence

ORD record
ord-0eb7fe62bfa0475795b1ec8c43594075
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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