3-Bromo-5-chloropyridin-2-amine → 3-Bromo-5-chloropyridin-2-ol

HRID 895884Notes

Reaction equation

HRID 895884 reaction equation
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.N([O-])=[O:11].[Na+]>O.Cl>[Br:8][C:7]1[C:2](=[O:11])[NH:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

5

Reactant 2

HCID 27639713-Bromo-5-chloropyridin-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 27267913-Bromo-5-chloropyridin-2-olYield 69%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 2-amino-3-bromo-5-chloropyridine (4.0 g, 19.3 mmol) in water (30 mL) and conc. HCl (5.2 mL) was cooled with an ice bath to 0° C. and was treated with a solution of sodium nitrite (1.33 g, 19.3 mmol) in water (12 mL) over 10 min. The mixture was stirred for an additonal 10 min and allowed to warm to room temperature over 48 hr. The mixture was filtered. The solids were washed with water, then with CCl4 and were dried under vacuum at 50° C. for 3 hr to give 3-bromo-5-chloro-1H-2-pyridone (2.77 g, 69%), mp 173.5-175° C.

Workup

  1. filtrationThe mixture was filtered
  2. washThe solids were washed with water
  3. dry with materialwith CCl4 and were dried under vacuum at 50° C. for 3 hr

Sources & evidence

ORD record
ord-b2917dd7b80e4ff69cc61f3d52649290
Source dataset
uspto-grants-2005_07
Patent number
US06916933B2

Reaction notes

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