Acetic Anhydride → 2-Acetamido-5-bromopyridine

HRID 2069841Notes

Reaction equation

HRID 2069841 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 2930972-Acetamido-5-bromopyridineYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 5-Bromo-pyridin-2-ylamine (100 mg, 0.578 mmol) in dry THF was added acetic anhydride (70.25 mg, 0.693 mmol). The reaction mixture was stirred at 20° C. for 12 hrs. THF was distilled out and to it was added ethyl acetate. The organic layer was washed with saturated NaHCO3 solution and dried over anhy sodium sulphate. Removal of the solvent afforded N-(5-Bromo-pyridin-2-yl)-acetamide (100 mg, 80%). This was carried to next step without further purification.

Workup

  1. distillationTHF was distilled out and to it
  2. additionwas added ethyl acetate
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. dry with materialdried over anhy sodium sulphate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-d092648319d4446c8b6e67ae31ae5bbc
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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