Pyridine → HCID 23438735, compound

HRID 1787901Notes

Reaction equation

HRID 1787901 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(=O)C([Cl:14])=O.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1.N1C=CC=CC=1>ClCCl.CN(C=O)C>[ClH:14].[NH2:1][C:2]1[C:3]([C:4]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=2)=[O:6])=[CH:7][CH:8]=[CH:9][N:10]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 661742-Amino-5-chloropyridineHCID 729302-Aminonicotinic acid

Product 1

HCID 23438735HCID 23438735, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring suspension of 2-aminonicotinic acid (26.9 g, 194 mmol) in dichloromethane (120 mL) at 0° C., was added DMF (a few drops), followed by oxalyl chloride (20 mL, 194 mmol). The cold bath was removed, and the solution was allowed to stir for 60 min at room temperature. This solution was then transferred via cannula into a stirring solution of 2-amino-5-chloropyridine (25 g, 194 mmol) and pyridine (78 mL, 970 mmol) in dichloromethane (100 mL). After stirring overnight, the precipitate was filtered and dried to give 32.8 g of solid. The crude product was recrystallized from ethanol with activated charcoal to give the amide (12.4 g, 23%) as a white solid.

Workup

  1. customThe cold bath was removed
  2. stirringAfter stirring overnight
  3. filtrationthe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-197def2531de41c1a5800dc10c81e8f3
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Reaction notes

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