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

HRID 323556Notes

Reaction equation

HRID 323556 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 96.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Trimethylacetyl chloride (39.2 mL, 0.32 mol) was added dropwise to a solution of compound 3 (27.3 g, 0.21 mol) in pyridine (100 mL). The resulting mixture was stirred overnight at ambient temperature. Water (200 mL) was added and the aqueous mixture was extracted with EtOAc (3×100 mL). The combined EtOAc extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to a solid which was crystallized from EtOH to give 43.2 g (95%) of compound 7 as a white solid.

Workup

  1. extractionthe aqueous mixture was extracted with EtOAc (3×100 mL)
  2. dry with materialThe combined EtOAc extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure to a solid which
  5. customwas crystallized from EtOH

Sources & evidence

ORD record
ord-b2196050b623498a9200e5e6973bfb25
Source dataset
uspto-grants-2001_04
Patent number
US06214801B1

Reaction notes

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