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

HRID 1260848
Notes
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Reaction equation

HRID 1260848 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Br:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1>CN(C)C=O>[BrH:11].[Cl:19][C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:10]1[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([NH2:6])=[O:5])[C:2]1=[NH:1]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 5066232-Aminopyridine-3-carboxamide

Product 1

HCID 686618971-(3-Chlorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromideYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-aminonicotinamide (0.1 g) in N,N-dimethylformamide (3 ml) was added 1-(bromomethyl)-3-chlorobenzene (0.3 g), and the mixture was stirred at 80° C. for 15 hr. The precipitated crystals were collected by filtration and washed with ethyl acetate to give the title compound (90 mg).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-3f284f2d52a6409190995c17568b0513
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08470859B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes