Furfurylamine → 2-[(2-Furylmethyl)amino]-6-methylnicotinic acid

HRID 2192769Notes

Reaction equation

HRID 2192769 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12]([NH2:18])[C:13]1[O:17][CH:16]=[CH:15][CH:14]=1>CN1CCCC1=O>[O:17]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:12][NH:18][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 3438FurfurylamineHCID 1217242-Chloro-6-methylnicotinic acid

Product 1

HCID 596252852-[(2-Furylmethyl)amino]-6-methylnicotinic acidYield 36%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-6-methylnicotinic acid (1.72 g) and furfurylamine (1.94 g) were dissolved in 1-methylpyrrolidin-2-one (25 ml), and the mixture was stirred at 150° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography. The fraction eluted with ethyl acetate-hexane (1:4-1:0) was concentrated under reduced pressure, and the precipitate was collected by filtration to give the object compound (838 mg) as a powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. washThe fraction eluted with ethyl acetate-hexane (1:4-1:0)
  4. concentrationwas concentrated under reduced pressure
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-b2a67844ab0b4877a04092dd34b8dd53
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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