3,5-Dichlorobenzyl chloride → 1-(3,5-Dichlorobenzyl)-2imino-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 1260850Notes

Reaction equation

HRID 1260850 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:13]=[C:14]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:15]Cl>CN(C)C=O.C(OCC)(=O)C>[ClH:11].[Cl:11][C:12]1[CH:13]=[C:14]([CH:17]=[C:18]([Cl:20])[CH:19]=1)[CH2:15][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 1378803,5-Dichlorobenzyl chlorideHCID 5066232-Aminopyridine-3-carboxamide

Product 1

HCID 686621591-(3,5-Dichlorobenzyl)-2imino-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 37.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-aminonicotinamide (0.18 g) in N,N-dimethylformamide (3 ml) was added 3,5-dichlorobenzyl chloride (0.31 g), 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 (0.10 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-4580c069e29547a39ee614947f9af06b
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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