N-bromobutanimide → HCID 22677333, compound

HRID 1837462Notes

Reaction equation

HRID 1837462 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([O:21]CC)=[CH2:20])[N:16]=[C:15]([C:24]([O:26][CH3:27])=[O:25])[C:14]=1[Cl:28])(=[O:11])[CH3:10]>C1COCC1.O>[C:9]([NH:12][C:13]1[CH:18]=[C:17]([C:19](=[O:20])[CH2:21][Br:1])[N:16]=[C:15]([C:24]([O:26][CH3:27])=[O:25])[C:14]=1[Cl:28])(=[O:11])[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22677378HCID 22677378, compound

Product 1

HCID 22677333HCID 22677333, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-Bromosuccinimide (0.377 g, 2.13 mmol) was added all at once to a solution of methyl 4-acetamido-3-chloro-6-(1-ethoxyvinyl)pyridine-2-carboxylate (0.636 g, 2.13 mmol) in THF (40 mL) and water (2 mL) at room temperature. After 15 minutes, the reaction mixture was concentrated and the residue partitioned between dichloromethane and water. The organic layer was separated, dried (MgSO4), and concentrated to provide methyl 4-acetamido-3-chloro-6-(bromoacetyl)pyridine-2-carboxylate (0.714 g, 2.04 mmol). 1H NMR (CDCl3): δ 9.12 (s, 1H), 7.99 (br.s, 1H), 4.82 (s, 2H), 4.06 (s, 3H), 2.36 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue partitioned between dichloromethane and water
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2a04ba0569a74eb5808f83352028a00d
Source dataset
uspto-grants-2004_08
Patent number
US06784137B2

Reaction notes

Loading…