4-(Aminomethyl)-1-methylpyridin-2(1H)-one → HCID 178480332, compound

HRID 2236848Notes

Reaction equation

HRID 2236848 reaction equation
[I: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])/[C:5]/2=[CH:14]/OC.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][N:22]([CH3:25])[C:21](=[O:26])[CH:20]=1>CN(C)C=O.O>[I: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])/[C:5]/2=[CH:14]\[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][N:22]([CH3:25])[C:21](=[O:26])[CH:20]=1

Participants

5

Reactant 2

HCID 220612874-(Aminomethyl)-1-methylpyridin-2(1H)-oneHCID 68691018(E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione

Product 1

HCID 178480332HCID 178480332, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(4E)-6-iodo-4-(methoxymethylene)isoquinoline-1,3(2H,4H)-dione (130 mg, 0.40 mmol), 4-aminomethyl-1-methyl-1H-pyridin-2-one (55 mg, 0.40 mol) were coupled in N,N-dimethylformamide (2 mL) at room temperature. The reaction mixture is diluted with water and the precipitate is collected by Büchner filtration and then dried under house vacuum to give (4Z)-6-iodo-4-({[(1-methyl-2-oxo-1,2-dihydropyridin-4-yl)methyl]amino}methylene)isoquinoline-1,3(2H,4H)-dione as an orange solid (0.15 g, 88%).

Workup

  1. filtrationthe precipitate is collected by Büchner filtration
  2. customdried under house vacuum

Sources & evidence

ORD record
ord-49d5d93f6cdc41d0a17a54da7a4c8299
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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