2-Aminopyridine-3-carboxamide → 1-(2,5-Dichlorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide

HRID 1260849Notes

Reaction equation

HRID 1260849 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][C:12]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=1[CH2:14][Br:15]>CN(C)C=O.C(OCC)(=O)C>[BrH:15].[Cl:11][C:12]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=1[CH2:14][N:10]1[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2]1=[NH:1]

Participants

5

Reactant 2

HCID 5066232-Aminopyridine-3-carboxamideHCID 34957442,5-Dichlorobenzyl bromide

Product 1

HCID 686623991-(2,5-Dichlorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromideYield 38.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-aminonicotinamide (0.2 g) in N,N-dimethylformamide (5 ml) was added 2,5-dichlorobenzylbromide (0.39 g) (Table 2, bromide 122), and the mixture was stirred at 80° C. for 14 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 (0.21 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-d0b1c3f3a6d34ae09698d54ec5016104
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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