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

HRID 1936447Notes

Reaction equation

HRID 1936447 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-82a1c99ba150438ebec8df9666cd43f7
Source dataset
uspto-grants-2002_05
Patent number
US06388084B1

Reaction notes

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