Benzylamine → 2-(Benzylamino)nicotinic acid

HRID 895292Notes

Reaction equation

HRID 895292 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C=O.[Cu]Br>[CH2:17]([NH:24][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acid

Product 1

HCID 2145962-(Benzylamino)nicotinic acid

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (4.82 g, 34.9 mmol) was added to a mixture of 2-chloronicotinic acid (5.0 g, 31.7 mol), benzylamine (3.47 ml, 31.7 mmol) and copper (I) bromide (450 mg, 3.17 mmol) in N,N-dimethylformamide (50 ml), and the reaction heated at 100° C. for 2 hours, then cooled. The resulting solid was filtered off and the filtrate evaporated under reduced pressure. The residue was partitioned between 4N sodium hydroxide solution (25 ml) and dichloromethane (25 ml) and the layers separated. The organic solution was extracted with water (2×), and the combined aqueous solutions, neutralised using concentrated hydrochloric acid. The resulting solid was filtered off, washed with cold water and dried in vacuo at 50° C., to afford the title compound, 1.6 g.

Workup

  1. temperaturecooled
  2. filtrationThe resulting solid was filtered off
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was partitioned between 4N sodium hydroxide solution (25 ml) and dichloromethane (25 ml)
  5. customthe layers separated
  6. extractionThe organic solution was extracted with water (2×)
  7. filtrationThe resulting solid was filtered off
  8. washwashed with cold water
  9. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-da735bcdfcb441d594c944ca3f350adc
Source dataset
uspto-grants-2005_07
Patent number
US06914160B1

Reaction notes

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