Dimethylformamide → N-[(4E)-1,3-Dioxo-4-(methoxy)methylene-1,2,3,4-tetrahydroisoquinolin-6-yl]acetamide

HRID 2236561Notes

Reaction equation

HRID 2236561 reaction equation
[NH2:1][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.CC(O[C:18]([CH3:20])=[O:19])=O.CN(C)C=O.[CH:26](OC)(OC)[O:27][CH3:28]>CCOCC>[O:12]=[C:8]1[C:9]2[C:4](=[CH:3][C:2]([NH:1][C:18](=[O:19])[CH3:20])=[CH:11][CH:10]=2)/[C:5](=[CH:26]\[O:27][CH3:28])/[C:6](=[O:13])[NH:7]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 116224226-Aminoisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 59300047N-[(4E)-1,3-Dioxo-4-(methoxy)methylene-1,2,3,4-tetrahydroisoquinolin-6-yl]acetamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 90 mg (0.50 mmol) of 6-aminoisoquinoline-1,3(2H,4H)-dione, 0.80 ml (8.5 mmol) of Ac2O, and 0.20 ml of N,N-DIMETHYLFORMAMIDE (DMF) is added 0.11 ml 1.0 mmol) of trimethyl orthoformate. The mixture is heated to 125° and maintained for 30 m, cooled, diluted with ether, and stirred for 10 m. The resulting amber solid is filtered, washed with ether, and dried to give 96 mg (74%); MS (ES+) m/z 261.1 (M+H)+1.

Workup

  1. temperatureThe mixture is heated to 125°
  2. temperaturemaintained for 30 m
  3. temperaturecooled
  4. filtrationThe resulting amber solid is filtered
  5. washwashed with ether
  6. customdried
  7. customto give 96 mg (74%)

Sources & evidence

ORD record
ord-f1868e2808634e9680bc94a7ead70871
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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