Benzyl Bromide → Benzyl 6-aminopyridine-3-carboxylate

HRID 2402309Notes

Reaction equation

HRID 2402309 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([O:16][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([NH2:9])=[N:11][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 184966-Aminonicotinic acid

Product 1

HCID 45790947Benzyl 6-aminopyridine-3-carboxylateYield 53.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (0.86 ml, 7.9 mmol) was added to a mixture of 6-aminonicotinic acid (1.0 g, 7.2 mmol) and potassium carbonate (1.5 g, 10.8 mmol) in DMF (4 mL). The mixture was stirred at room temperature for 16 hr and diluted with water (50 mL). The aqueous mixture was extracted with ethyl acetate (1×). The EtOAc layer was washed with brine, dried over MgSO4 and concentrated to provide crude solid product. Recrystallization from diethyl ether provided the title compound as a pale yellow solid (0.88 g, 53%).

Workup

  1. extractionThe aqueous mixture was extracted with ethyl acetate (1×)
  2. washThe EtOAc layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto provide crude solid product
  6. customRecrystallization from diethyl ether

Sources & evidence

ORD record
ord-347978c0d2ce4815a3c492a313de4ede
Source dataset
uspto-grants-2014_08
Patent number
US08796313B2

Reaction notes

Loading…