Water → 4-Amino-3-bromo-6-chloropyridine-2-carboxylic acid
Reaction equation
[Br:1][C:2]1[C:3]([C:10]([O:12]C)=[O:11])=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1Cl.[N-:14]=[N+]=[N-].[Na+].O.[BH4-].[Na+]>CN(C=O)C.CO>[NH2:14][C:7]1[CH:6]=[C:5]([Cl:9])[N:4]=[C:3]([C:10]([OH:12])=[O:11])[C:2]=1[Br:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
To a solution of methyl 3-bromo-4,6-dichloropyridine-2-carboxylate (0.9 g, 3.2 mmol) in aqueous DMF was added NaN3 (0.25 g, 3.8 mmol). The resulting mixture was heated at 60° C. for 1 hr, added to H2O and extracted (3×) with Et2O. Organic layer was concentrated to yield a white solid, which was dissolved in 10 mL of MeOH. Excess NaBH4 was added and the reaction mixture stirred at room temperature for 0.5 hr. This material was added to H2O, extracted (3×) with Et2O, dried over MgSO4 and concentrated. The resulting solid was stirred in 1N NaOH for 1 hr, made acidic with conc. HCl and concentrated to dryness. This material was extracted with MeOH, concentrated to give 220 mg of 4-amino-3-bromo-6-chloropyridine-2-carboxylic acid; mp 175° C. dec.
Workup
- extractionextracted (3×) with Et2O
- concentrationOrganic layer was concentrated
- customto yield a white solid, which
- extractionextracted (3×) with Et2O
- dry with materialdried over MgSO4
- concentrationconcentrated
- stirringThe resulting solid was stirred in 1N NaOH for 1 hr
- concentrationconcentrated to dryness
- extractionThis material was extracted with MeOH
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d884f744f697402bba834ccf0ab9ae98
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06297197B1
Reaction notes
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