1-(Bromomethyl)-3-chlorobenzene → 1-(3-Chlorobenzyl)-2-imino-5-methyl-1,2-dihydropyridine-3-carboxamide hydrobromide

HRID 1260860Notes

Reaction equation

HRID 1260860 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][Br:17]>CN(C)C=O.C(OCC)(=O)C>[BrH:17].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][N:10]1[CH:9]=[C:8]([CH3:11])[CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2]1=[NH:1]

Participants

5

Reactant 2

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 668782802-Amino-5-methylnicotinamide

Product 1

HCID 686617751-(3-Chlorobenzyl)-2-imino-5-methyl-1,2-dihydropyridine-3-carboxamide hydrobromideYield 42.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-amino-5-methylnicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-chlorobenzylbromide (0.31 g), and the mixture was stirred at 100° C. for 6 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (0.15 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. customThe obtained precipitate was recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-3bd7219d438444a5bbed78ca8a8add6b
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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