Hydrochloric Acid → 3-Amino-5-bromopyridine-2-carboxylic acid

HRID 2284400Notes

Reaction equation

HRID 2284400 reaction equation
[NH2:1][C:2]1[C:3]([C:9](N)=[O:10])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[OH-:12].[Na+].Cl>>[NH2:1][C:2]1[C:3]([C:9]([OH:10])=[O:12])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 210758623-Amino-5-bromopyridine-2-carboxamide

Product 1

HCID 497615813-Amino-5-bromopyridine-2-carboxylic acidYield 95%

Procedure

To a 100 mL round bottom flask, 3-amino-5-bromo-pyridine-2-carboxylic acid amide (1.05 g, 0.0049 mol) and aqueous sodium hydroxide solution (0.98 g in 10 mL water, 0.0245 mol) were added. The reaction mixture was stirred at reflux temperature for 5 hours. The volatiles were evaporated under reduced pressure to provide the residue. The residue was neutralized to pH 7.0, using 2N HCl at 0° C. to obtain the precipitate. The precipitate was filtered and dried to provide the title compound as light yellow solid (1 g, 95%). 1H NMR (300 MHz, DMSO-d6): δ 7.65 (d, J=2.1 Hz, 1H), 7.20 (d, J=2.1 Hz, 1H), 7.01-7.16 (br s, 2H); LC-MS (ESI): Calculated mass: 216.0; Observed mass [M+H]+: 217.0. (RT: 0.43 min).

Workup

  1. temperatureat reflux temperature for 5 hours
  2. customThe volatiles were evaporated under reduced pressure
  3. customto provide the residue
  4. customat 0° C.
  5. customto obtain the precipitate
  6. filtrationThe precipitate was filtered
  7. customdried

Sources & evidence

ORD record
ord-e2a85e53d3334f34ad9bb03cd8c97688
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

Loading…