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

HRID 1987026Notes

Reaction equation

HRID 1987026 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1.[CH3:16][C:17]([CH3:22])([CH3:21])[C:18](Cl)=[O:19]>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:18](=[O:19])[C:17]([CH3:22])([CH3:21])[CH3:16])[CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 10656204N-(4-Chloropyridin-2-yl)pivalamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (6.8 mL, 48.6 mmol) was added to a stirred solution of 4-chloro-2-aminopyridine, 11, (Townsend, L. B. et al Synthetic Commun. 1997 27, 861-870) (5 g, 38.9 mmol) in dichloromethane (75 mL). After cooling to 0° C. a solution of trimethylacetyl chloride (5.3 mL, 42.8 mmol) in dichloromethane (10 mL) was added dropwise over 15 min. The mixture was allowed to warm to 23° and stirred for 18 h then washed with saturated sodium bicarbonate. The organic layer was dried (Na2SO4) and evaporated in vacuo to give an off-white solid. This was recrystallised from isopropyl ether to afford the title compound as white crystals (5.5 g, 67%). MS(EI) m/e 213, 215 [M+H]+.

Workup

  1. additionwas added dropwise over 15 min
  2. temperatureto warm to 23°
  3. washthen washed with saturated sodium bicarbonate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give an off-white solid
  7. customThis was recrystallised from isopropyl ether

Sources & evidence

ORD record
ord-f328a3a4146b4d3ca1cf2e21b97e1e54
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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