Hydrochloric Acid → 2-Amino-5-bromo-3-hydroxypyridine

HRID 434331Notes

Reaction equation

HRID 434331 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[O:10]C(=O)[NH:8][C:5]2=[N:6][CH:7]=1.[OH-].[Na+].Cl>O>[NH2:8][C:5]1[C:4]([OH:10])=[CH:3][C:2]([Br:1])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 136144586-Bromo-3H-oxazolo(4,5-b)pyridin-2-one

Product 1

HCID 116940412-Amino-5-bromo-3-hydroxypyridineYield 52.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

6-Bromooxazolo[4,5-b]pyridine-2(3H)-one (K. Rufenacht and H. Kristinsson, Helv. Chim. Acta 59 (5), 1593 [1976]) (4.3 g; 0.02 mole) sodium hydroxide (5 g; 0.125 mole) and water (50 ml) were stirred on the steam bath for 45 minutes. The solution was cooled to approximately 10° C. and carefully acidified with concentrated HCl (considerable foaming). The resulting solid was collected by filtration, washed with water and dried. The yield was 3.0 g (79 percent) of tan solid melting at 187° to 189° C. Recrystallization from aqueous ethanol afforded 2.0 g of tan crystals, melting point 195° to 197° C.

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with water
  3. customdried
  4. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-1b87cd000aee4ec88572b549be5549dc
Source dataset
uspto-grants-1983_08
Patent number
US04396546

Reaction notes

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