Sodium Hydroxide → 2-Amino-5-bromopyridine-3-sulfonic acid

HRID 241064Notes

Reaction equation

HRID 241064 reaction equation
[NH2:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[OH-:13].[Na+]>O1CCOCC1>[NH2:1][C:2]1[C:7]([S:8]([OH:13])(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 866478252-Amino-5-bromopyridine-3-sulfonic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

2-Amino-5-bromopyridine-3-sulfonyl chloride (100 mg, 0.37 mmol) was taken into 1:1 aqueous dioxane (3 mL) and the mixture was basified to pH 14 by drop wise addition of 50% aqueous sodium hydroxide solution. The mixture was warmed to 75° C. for 0.5 h then cooled to room temperature and concentrated. The residue was taken into water (2 mL) and carefully acidified to pH 1-2 by concentrated aqueous hydrochloric acid addition and cooled to 0° C. After 1 h at 0° C. the crystalline solid obtained was collected by filtration and dried to give 2-amino-5-bromopyridine-3-sulfonic acid as a solid. 1H NMR (DMSO-d6): 8.24 (d, 1H), 8.06 (d, 1H). MS (EI) for C5H5N2SO3Br: 253, 255 (MH+, Br pattern).

Workup

  1. temperaturethen cooled to room temperature
  2. concentrationconcentrated
  3. additioncarefully acidified to pH 1-2 by concentrated aqueous hydrochloric acid addition
  4. temperaturecooled to 0° C
  5. customAfter 1 h at 0° C. the crystalline solid obtained
  6. filtrationwas collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-f8cb5c32d2c84011909a52935f052912
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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