2-Pyridinemethanamine → 6-Chloro-2-[(pyridin-2-ylmethyl)amino]nicotinic acid

HRID 1260581Notes

Reaction equation

HRID 1260581 reaction equation
Cl[C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>C(O)(C)(C)C>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:10]=1

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 8540472,6-Dichloronicotinic acid

Product 1

HCID 551843576-Chloro-2-[(pyridin-2-ylmethyl)amino]nicotinic acidYield 79%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

4 g of 2,6-dichloronicotinic acid (20.83 mmol, Aldrich) and 10.74 ml of 2-(aminomethyl)pyridine (104.17 mmol) are placed in an 80 ml sealed tube containing 40 ml of tert-butanol. The mixture is heated at 100° C. overnight and evaporated to dryness. The residue is taken up in water and the mixture is acidified by pouring in an aqueous solution of acetic acid at 10%. The precipitate is isolated by filtration and, after drying in an oven under a reduced vacuum, 4.35 g of expected product are obtained in the form of a yellow powder (yield=79%).

Workup

  1. customsealed tube
  2. customevaporated to dryness
  3. additionby pouring in an aqueous solution of acetic acid at 10%
  4. customThe precipitate is isolated by filtration
  5. dry with materialafter drying in an oven under a reduced vacuum, 4.35 g of expected product

Sources & evidence

ORD record
ord-9ac78a8833134967a89c290ee55b9f9e
Source dataset
uspto-grants-2013_06
Patent number
US08470847B2

Reaction notes

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