Acetic Acid → 2-Acetamido-5-bromopyridine

HRID 1432893Notes

Reaction equation

HRID 1432893 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][N:10]=1.[C:16](O)(=[O:18])[CH3:17]>>[Br:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:16](=[O:18])[CH3:17])=[N:10][CH:11]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 8471TriethylamineHCID 706222-Amino-5-bromopyridine

Product 1

HCID 2930972-Acetamido-5-bromopyridineYield 41.4%

Procedure

Triethylamine (17.7 mL, 75 mmol) is added to a mixture of 2-amino-5-bromopyridine (5.0 g, 29 mmol) and acetic acid (7.1 mL, 75 mmol). The solution is heated to reflux for 48 hours. After this time, the solution is concentrated. The reside is dissolved in water and the pH is adjusted to 10 with 1N NaOH. The solids are collected by filtration. The crude product is recrystallized from boiling water to give the title compound (2.6 g 12.0 mmol) as a white solid. 1H NMR (300 MHz, CDCl3) δ10.62 (1H, bs), 8.42 (s, 1H), 8.01 (m, 2H), 2.05 (s, 3H).

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux for 48 hours
  3. concentrationAfter this time, the solution is concentrated
  4. dissolutionThe reside is dissolved in water
  5. filtrationThe solids are collected by filtration
  6. customThe crude product is recrystallized

Sources & evidence

ORD record
ord-4d60c27083b44392aca1323be5c7bdec
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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