Methanol → Methyl 6-amino-5-bromonicotinate

HRID 976381Notes

Reaction equation

HRID 976381 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 dis-solved 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. filtrationthe solid which separates is filtered
  3. washwashed well with water and air
  4. customdried

Sources & evidence

ORD record
ord-3be82ede0ae34e88bd55c52ebd892f89
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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