Dimethylmethylenammonium chloride → 2-[(Dimethylamino)methyl]furo[2,3-c]isoquinolin-5(4H)-one hydrochloride

HRID 472677Notes

Reaction equation

HRID 472677 reaction equation
[CH:1]1[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:6](=[O:14])[NH:5][C:4]=2[O:3][CH:2]=1.[Cl-:15].[CH3:16][N+:17](=[CH2:19])[CH3:18]>CN(C)C=O.C(#N)C>[ClH:15].[CH3:16][N:17]([CH2:19][C:2]1[O:3][C:4]2[NH:5][C:6](=[O:14])[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[C:13]=2[CH:1]=1)[CH3:18]

Participants

5

Reactant 2

HCID 11051579Dimethylmethylenammonium chlorideHCID 58024727Furo[2,3-c]isoquinolin-5(4H)-one

Product 1

HCID 446009722-[(Dimethylamino)methyl]furo[2,3-c]isoquinolin-5(4H)-one hydrochlorideYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

Furo[2,3-c]isoquinolin-5(4H)-one (55 mg, 0.27 mmol) was dissolved in a mixture of dry dimethylformamide (1 ml) and dry acetonitrile (2 ml) and treated with N,N-dimethyl(methylene)ammonium chloride (1 mmol) prepared according to known procedure (Kinast G. et al. Angew. Chem. Int. Ed. Engl. 1976, 15(4), 239-240; Bohme H. et al. Chem. Ber. 1960, 93, 1305). The reaction mixture was refluxed overnight, and the resulting precipitate was filtered and washed with dry diethyl ether to give the title compound. Yield: 65%.

Workup

  1. customprepared
  2. temperatureThe reaction mixture was refluxed overnight
  3. filtrationthe resulting precipitate was filtered
  4. washwashed with dry diethyl ether

Sources & evidence

ORD record
ord-8e0890c25532482286492ef4712e5c39
Source dataset
uspto-grants-2014_01
Patent number
US08633215B2

Reaction notes

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