Acetic Acid → 2-Acetamido-5-bromopyridine

HRID 378563Notes

Reaction equation

HRID 378563 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.O.[OH-].[Na+].[C:12](O)(=[O:14])[CH3:13]>C(OC(=O)C)(=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:12](=[O:14])[CH3:13])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 2930972-Acetamido-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 25.0 g (144 mmol) of 2-amino-5-bromopyridine in 50 mL of acetic acid and 250 mL of acetic anhydride was heated at reflux for about 2 hours. The reaction mixture was then cooled and poured into 750 mL of water with stirring. After about 1 hour, the solution was adjusted to pH=10 with 50% sodium hydroxide solution and the precipitate was filtered, washed with water and dried to give 26.5 g of the title product as a white flaky solid, mp 175-176° C. 1H nmr (deuteriochloroform): δ=8.29 (d, 1 H); 8.12 (d, 1 H); 7.96 (br, 1 H); 7.78 (d of d, 1 H); 2.19 (s, 3 H). MS (El): m/z=214, 216 (M+, Br isotopes).

Workup

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

Sources & evidence

ORD record
ord-1689e7993af44ed99334b50a757d688f
Source dataset
uspto-grants-2000_02
Patent number
US06031105

Reaction notes

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