Water → Methyl 4-amino-6-bromo-3-methoxypicolinate

HRID 378790Notes

Reaction equation

HRID 378790 reaction equation
[N:1]([C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=1[O:15][CH3:16])=[N+]=[N-].[BH4-].[Na+].C(OCC)(=O)C.O>CO>[NH2:1][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 21696596Methyl 4-azido-6-bromo-3-methoxypyridine-2-carboxylate

Product 1

HCID 21696668Methyl 4-amino-6-bromo-3-methoxypicolinateYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 4-azido-6-bromo-3-methoxypyridine-2-carboxylate (0.500 g, 1.74 mmol) in 10 mL of methanol was added NaBH4 (0.046 g, 1.22 mmol). The reaction mixture was stirred at room temperature for 10 min. Ethyl acetate and water were added and the phases were separated. The organic phase was washed with H2O, dried (MgSO4) and concentrated to dryness in vacuo. The residue was purified by chromatography (silica gel). Elution with 100% ethyl acetate gave 0.300 g of a white solid. 1H NMR(CDCl3): δ 3.90 (s, 1H); 3.95 (s, 1H); 4.60 (s, 2H); 6.85 (s, 1H).

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with H2O
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness in vacuo
  5. customThe residue was purified by chromatography (silica gel)
  6. washElution with 100% ethyl acetate

Sources & evidence

ORD record
ord-f67d112592824055bec8951e8c7feabc
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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