Methanol → Methyl 6-amino-5-bromonicotinate

HRID 1457641Notes

Reaction equation

HRID 1457641 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[Br:11].[CH3:12]O.[OH-].[Na+]>Cl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:12])=[O:9])=[CH:4][C:3]=1[Br:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 227420286-Amino-5-bromo-nicotinic acid

Product 1

HCID 2764099Methyl 6-amino-5-bromonicotinate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6-Amino-5-bromopyridine-3-carboxylic acid (10 g, 50 mmol) is dissolved in saturated methanolic HCl (100 ml) and refluxed for 24 hours. The solvent, methanol, is re-moved under reduced pressure and the residue is dissolved in ice cold water. The aqueous solution is neutralized with 0.1N NaOH and the solid which separates is filtered; washed well with water and air dried to yield 10 g of product as a solid: mass spectrum 231 (M+).

Workup

  1. temperaturerefluxed for 24 hours
  2. dissolutionthe residue is dissolved in ice cold water
  3. filtrationthe solid which separates is filtered
  4. washwashed well with water and air
  5. customdried

Sources & evidence

ORD record
ord-ce4854c14df341fca3c4593b3ddd9cc0
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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