Water → N-(4-Chloropyridin-2-yl)pivalamide

HRID 556836Notes

Reaction equation

HRID 556836 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[NH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][N:10]=1.O>N1C=CC=CC=1>[Cl:15][C:13]1[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 62493Pivaloyl chlorideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 10656204N-(4-Chloropyridin-2-yl)pivalamideYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trimethylacetyl chloride (4.22 g, 35.0 mmol) was added dropwise to a solution of 2-amino-4-chloropyridine (3.00 g, 23.3 mmol) in pyridine (11 mL) at 0° C. The resulting solution was stirred for 12 h at r.t. Water (20 mL) was added and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried (MgSO4). The solvent was removed in vacuo and the crude mixture was purified by flash chromatography on silica, eluting with ethyl acetate and hexane (2/8), to give the title compound as a colourless solid (4.9 g, 99%).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×10 mL)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. customThe solvent was removed in vacuo
  4. customthe crude mixture was purified by flash chromatography on silica
  5. washeluting with ethyl acetate and hexane (2/8)

Sources & evidence

ORD record
ord-907a4138d3914b03a4af02f0ff307635
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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