Dimethylformamide → (4E)-4-(Methoxymethylene)-6-nitroisoquinoline-1,3(2H,4H)-dione

HRID 2236558Notes

Reaction equation

HRID 2236558 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[NH:9][C:8](=[O:15])[CH2:7]2)([O-:3])=[O:2].C[C:17]([O:19][C:20](C)=O)=O.CN(C)C=O.C(OC)(OC)OC>CCOCC>[CH3:17][O:19]/[CH:20]=[C:7]1/[C:8](=[O:15])[NH:9][C:10](=[O:14])[C:11]2[C:6]/1=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:13][CH:12]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 592999676-nitroisoquinoline-1,3(2H,4H)-dione

Product 1

HCID 59300161(4E)-4-(Methoxymethylene)-6-nitroisoquinoline-1,3(2H,4H)-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 0.41 g (2.0 mmol) of 6-nitroisoquinoline-1,3(2H,4H)-dione, 3.2 ml (34 mmol) of Ac2O, and 0.80 ml of N,N-DIMETHYLFORMAMIDE is added 0.44 ml (4.0 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 brown solid is filtered, washed with ether, and dried to give 372 mg (74%); 1H NMR (DMSO-d6) δ 11.55 (s, 1H), 8.99 (d, J=2.0 Hz, 1H), 8.30 (d, J=8.6 Hz, 1H), 8.19 (dd J=2.0, 8.6 Hz, 1H), 4.33 (s, 3H).

Workup

  1. temperatureThe mixture is heated to 125°
  2. temperaturemaintained for 30 m
  3. temperaturecooled
  4. filtrationThe resulting brown solid is filtered
  5. washwashed with ether
  6. customdried
  7. customto give 372 mg (74%)

Sources & evidence

ORD record
ord-294886baeb74427484de52b90231748e
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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