Benzylamine → 2-(Benzylamino)nicotinic acid

HRID 901226Notes

Reaction equation

HRID 901226 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13]>N1C=CC=CC=1>[CH2:1]([NH:8][C:10]1[N:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 762582-Chloronicotinic acid

Product 1

HCID 2145962-(Benzylamino)nicotinic acidYield 84.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzylamine (14 mL, 126.8 mmol) was added to a solution of chloronicotinic acid (10 g, 63.4 mmol) in pyridine and refluxed overnight. The pyridine was distilled and the residue was dissolved in 1N NaOH. The solution was diluted with water to adjust the pH to 10 to 11 and washed by dichloromethane. The aqueous phase was neutralized with cold aqueous 10% HCl solution to adjust the pH to 6 to 7. The solids formed were filtered, washed with cold water, and dried in a vacuum oven to yield 12.2 g (84%) of 2-benzylamino nicotinic acid (1) as white solids. MP: 148° C.; 1H-NMR (DMSO-d6): δ 4.69 (d, J=3.6 Hz, 2H), 6.61 (dd, J=4.9, 7.7 Hz, 1H), 7.23 (m, 1H), 7.29 (m, 4H), 8.08 (dd, J=1.8, 7.0 Hz, 1H), 8.28 (dd, J=1.8, 7.0 Hz, 1H), 8.47 (br. s, 1H), 13.10 (s, 1H); EIMS: 229 (M+1), 251 (M+23).

Workup

  1. temperaturerefluxed overnight
  2. distillationThe pyridine was distilled
  3. dissolutionthe residue was dissolved in 1N NaOH
  4. additionThe solution was diluted with water
  5. washwashed by dichloromethane
  6. customThe solids formed
  7. filtrationwere filtered
  8. washwashed with cold water
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-e75edce2d7cb4316899e54b949f604b4
Source dataset
uspto-grants-2008_04
Patent number
US07361760B2

Reaction notes

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