2-Chloronicotinic acid → 2-[[2-[[(4-Methyl-1H-imidazol-5-yl)methyl]thio]ethyl]amino]-3-pyridinecarboxylic acid

HRID 1906465Notes

Reaction equation

HRID 1906465 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].Cl[C:13]1[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1>O.[OH-].[Na+]>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:13]1[C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

5

Reactant 2

HCID 762582-Chloronicotinic acidHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Product 1

HCID 155952552-[[2-[[(4-Methyl-1H-imidazol-5-yl)methyl]thio]ethyl]amino]-3-pyridinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

An intimate mixture of powdered 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.71 g; 0.010 moles) and 2-chloropyridine-3-carboxylic acid (1.73 g; 0.011 moles) was heated to 150° for 6 hours. The resulting cooled glass was dissolved in a little water and neutralised by slow addition of 2N sodium hydroxide solution. At pH6, solid precipitated out of solution. This was filtered off, and recrystallised from water to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino pyridine 3-carboxylic acid as small, colourless crystals (1.04 g) which sublimed at 98°.

Workup

  1. temperaturewas heated to 150° for 6 hours
  2. temperatureThe resulting cooled glass
  3. customAt pH6, solid precipitated out of solution
  4. filtrationThis was filtered off
  5. customrecrystallised from water

Sources & evidence

ORD record
ord-fe03a8daca0f472d8fc144ab34feb0e6
Source dataset
uspto-grants-1987_03
Patent number
US04652572

Reaction notes

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