Dimethylformamide dimethyl acetal → (4E)-4-[(Dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinone

HRID 2236405Notes

Reaction equation

HRID 2236405 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3](=[O:11])[NH:2]1.CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>CN(C)C=O>[CH3:14][N:15](/[CH:17]=[C:4]1/[C:3](=[O:11])[NH:2][CH2:1][C:10]2[C:5]/1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:16]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 904691,4-dihydro-2H-isoquinolin-3-one

Product 1

HCID 68694591(4E)-4-[(Dimethylamino)methylene]-1,4-dihydro-3(2H)-isoquinolinoneYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A N,N-dimethylformamide (1 mL) solution containing 1,4-dihydro-3(2H)-isoquinolinone (300 mg, 2.04 mmol) and N,N-dimethylformamide dimethylacetal (0.65 mL, 4.89 mmol) is heated at 100° C. for 2.5 hours. After removing the solvents, the residue is washed with ether, water and ether to give 88 mg of the product as a pink solid. The filtrate is evaporated to dryness, and the residue is treated with ether, water and ether to give 105 mg of a second crop of the product with a total yield of 47% (193 mg); MS (ESI) m/z 203.2 (M+1). Ref: Chemistry of Heterocyclic compd. 370-374 (1981).

Workup

  1. customAfter removing the solvents
  2. washthe residue is washed with ether, water and ether

Sources & evidence

ORD record
ord-69e8a571326d40a7ae73e5c18c7ade83
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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