Hydrochloric Acid → HCID 67469678, compound

HRID 1522594Notes

Reaction equation

HRID 1522594 reaction equation
[C:1]([N:4]([C:8]1[C:9]([CH3:15])=[N:10][CH:11]=[CH:12][C:13]=1[Br:14])C(=O)C)(=[O:3])[CH3:2].[OH-].[Na+].Cl>CO>[Br:14][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:15])[C:8]=1[NH:4][C:1](=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67469677HCID 67469677, compound

Product 1

HCID 67469678HCID 67469678, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-acetyl-N-(4-bromo-2-methylpyridin-3-yl)acetamide (0.95 g, 3.50 mmol) in methanol (14.02 mL) was added 1M NaOH (0.876 ml, 0.876 mmol) and the reaction was stirred at room temperature for 30 minutes. The reaction mixture was neutralized with 1N HCl (400 uL) and then concentrated under vacuum to give a residue that was purified on silica column chromatography eluting with (chloroform:methanol, 97:3) Concentration of the product fractions gave N-(4-bromo-2-methylpyridin-3-yl)acetamide (0.7 g, 3.06 mmol, 87% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.04-2.10 (m, 3H) 2.39 (s, 3H) 7.49-7.60 (m, 1H) 8.12-8.26 (m, 1H) 9.65-9.83 (m, 1H). MS [M+H] found 229.1.

Workup

  1. concentrationconcentrated under vacuum
  2. customto give a residue that
  3. customwas purified on silica column chromatography
  4. washeluting with (chloroform:methanol, 97:3) Concentration of the product fractions

Sources & evidence

ORD record
ord-a11891aa8d4c45798f3d3af39ef86eb0
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

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