N-bromobutanimide → Ethyl 5-amino-6-bromo-2-methylnicotinate

HRID 906183Notes

Reaction equation

HRID 906183 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].C1C(=O)N([Br:21])C(=O)C1>CN(C=O)C.O>[NH2:1][C:2]1[C:3]([Br:21])=[N:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22180329Ethyl 5-amino-2-methylnicotinate

Product 1

HCID 71464138Ethyl 5-amino-6-bromo-2-methylnicotinateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-amino-2-methylnicotinate (Fanta, P. E. J. Am. Chem. Soc. 1953, 75, 737) (4.1 g, 22.78 mmol) in DMF (50 ml) was added NBS (4.46 g, 25.06 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with water (100 ml) and then extracted with ethyl acetate (3×100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate and brine. After evaporation of solvent, the residue was triturated with ethanol to give ethyl 5-amino-6-bromo-2-methylnicotinate. (5.2 g, 88% yield). 1H NMR (400 MHz, CDCl3): 7.56 (s, 1H), 4.40 (q, J=6.8 Hz, 2H), 4.05 (br, s, 2H), 2.75 (s, 3H), 1.39 (t, J=6.8 Hz, 3H). MS (EI) for C9H1BrN2O2: 259.1 (MH+).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  3. customAfter evaporation of solvent
  4. customthe residue was triturated with ethanol

Sources & evidence

ORD record
ord-569a41ec6ca94096a77e8d9bec288813
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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