Water → 2-Acetamido-5-bromopyridine

HRID 431266Notes

Reaction equation

HRID 431266 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10].O.[OH-].[Na+]>C(O)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:9](=[O:11])[CH3:10])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 2930972-Acetamido-5-bromopyridineYield 85.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 2-amino-5-bromopyridine (25.0 g, 144 mmol) in acetic acid (50 ml) and acetic anhydride (25.0 g) was heated at reflux for two hours. The reaction mixture was then cooled and poured into water (750 ml) with stirring. After one hour, the solution was adjusted to pH 10 with 50% sodium hydroxide and the precipitate was filtered, washed with water and dried to give 26.5 g (85%) of the title product as a white flaky solid. mp 175-176° C. 1H NMR (CDCl3): δ=8.29 (d, 1H); 8.12 (d, 1H); 7.96 (br, 1H); 7.78 (d of d, 1H); 2.19 (s, 3H). MS (EI): m/z=214, 216 (M+, Br isotopes).

Workup

  1. temperatureat reflux for two hours
  2. temperatureThe reaction mixture was then cooled
  3. filtrationthe precipitate was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-449724e6afef4c9bb80f4441b1af274d
Source dataset
uspto-grants-2003_12
Patent number
US06657063B1

Reaction notes

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