Acetyl chloride → N-(6-bromopyridin-2-yl)acetamide

HRID 2420872Notes

Reaction equation

HRID 2420872 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[C:16](Cl)(=[O:18])[CH3:17]>C(Cl)Cl.O>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:16](=[O:18])[CH3:17])[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 10353221N-(6-bromopyridin-2-yl)acetamideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromopyridin-2-amine (10 g, 0.060 mol) and Et3N (25 g, 0.27 mol) in CH2Cl2 (300 mL) was added acetyl chloride (13 g, 0.17 mol) at 0° C. The mixture was stirred overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (200 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under vacuum to give N-(6-bromopyridin-2-yl)acetamide (11 g, 88%). 1H NMR (400 MHz, CDCl3) □ 8.15 (d, J=8.0 Hz, 1H), 7.97 (brs, 1H), 7.55 (t, J=8.0 Hz, 1H), 7.18 (d, J=8.0 Hz, 1H), 2.19 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (200 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-8cc2fa059afd44baae93ee6177e29099
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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