Water → Methyl 2-amino-5-bromonicotinate

HRID 646724

Reaction equation

HRID 646724 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.OS(O)(=O)=O.O.[C:18](=O)([O-])[O-].[Na+].[Na+]>CO.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([C:8]([O:10][CH3:18])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 7374452-Amino-5-bromonicotinic acid

Product 1

HCID 2763453Methyl 2-amino-5-bromonicotinateYield 73.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A slurry of 2-amino-5-bromopyridine-3-carboxylic acid (7 g, 32.2 mmol) in methanol (150 mL) and H2SO4 (7 mmol) was heated to reflux for 48 h. The reaction mixture was concentrated to ca. 40 mL. Water (100 mmol) was added to the residual oil, and the mixture neutralized with sodium carbonate. Ethyl acetate (400 mL) was added and the organic layer was washed with saturated aqueous sodium chloride then dried (Na2SO4) and concentrated to give the title compound (5.5 g, 73.9% yield).

Workup

  1. temperatureto reflux for 48 h
  2. concentrationThe reaction mixture was concentrated to ca. 40 mL
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialthen dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-43ab49ea88d541d0b6298495788b4593
Source dataset
uspto-grants-2010_04
Patent number
US07704995B2

Linked notes

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