Dimethylamine → 4-chloro-N,N-dimethylpyridine-2-carboxamide

HRID 1915698Notes

Reaction equation

HRID 1915698 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](Cl)=[O:9])[CH:3]=1.[CH2:11]([N:13](CC)[CH2:14]C)C.CNC>ClCCl>[CH3:11][N:13]([CH3:14])[C:8]([C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][N:5]=1)=[O:9]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 110951464-chloropyridine-2-carbonyl Chloride

Product 1

HCID 49622524-chloro-N,N-dimethylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-pyridine-2-carbonyl chloride (1 eq) in dichloromethane was cooled to 0° C., whereupon triethylamine (2 eq) was added followed by dimethylamine (2 eq, 2M solution in THF). The solution was allowed to warm to room temperature and let stir overnight. It was then washed with 1M NaOH. The separated organic layer is dried over MgSO4, filtered, and concentrated to yield the desired product. HPLC, 1.82 min; MS: MH+=185.6

Workup

  1. additionwas added
  2. washIt was then washed with 1M NaOH
  3. dry with materialThe separated organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a26aed881c1a4639998d9465be00d380
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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