Hydrogen Bromide → Methyl 2-bromo-3-(2-methoxy-5-pyridyl)propionate

HRID 322314Notes

Reaction equation

HRID 322314 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[BrH:10].N([O-])=O.[Na+].[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17]>O.CC(C)=O>[Br:10][CH:16]([CH2:17][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1)[C:15]([O:19][CH3:20])=[O:18]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 811216-Methoxy-3-pyridinylamineHCID 23668193Sodium Nitrite

Product 1

HCID 22009772Methyl 2-bromo-3-(2-methoxy-5-pyridyl)propionateYield 58%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of 5-amino-2-methoxypyridine (5.00 g), 47% hydrobromic acid (8.75 g) and acetone (50 ml) was added dropwise a solution of sodium nitrite (3.06 g) in water (5 ml) at 5-10° C. After stirring for 30 minutes, methyl acrylate (20.8 g) was added, to which cuprous oxide (50 mg) was added while stirring vigorously at 15° C. After stirring for one hour at room temperature, the reaction mixture was concentrated, concentrated aqueous ammonia was added, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduce pressure. The residue was subjected to a silica gel chromatography. From the fraction eluted with ethyl acetate-hexane (1:9, v/v), methyl 2-bromo-3-(2-methoxy-5-pyridyl)propionate (6.40 g, 58%) was obtained. Oily substance.

Workup

  1. additionwas added
  2. stirringwhile stirring vigorously at 15° C
  3. stirringAfter stirring for one hour at room temperature
  4. concentrationthe reaction mixture was concentrated
  5. additionconcentrated aqueous ammonia was added
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate layer was washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. washFrom the fraction eluted with ethyl acetate-hexane (1:9, v/v)

Sources & evidence

ORD record
ord-cd043009112c44eba1f9e553cb9a58dc
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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