Methyl 6-chloropyridine-3-carboxylate → Methyl 6-(dimethylamino)pyridine-3-carboxylate

HRID 507293Notes

Reaction equation

HRID 507293 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[CH3:12][NH:13][CH3:14].CO>>[CH3:12][N:13]([CH3:14])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 22497844Dimethylamine methanol

Product 1

HCID 23271116Methyl 6-(dimethylamino)pyridine-3-carboxylateYield 98.9%

Procedure

A solution of methyl 6-chloronicotinate (4.0 g, 23 mmol) in dimethylamine/MeOH (2 M, 80 mL, 160 mmol) in a pressure vessel was stirred at 95° C. for 2 h, cooled to rt and concentrated. The residue was dissolved in EtOAc (250 mL), washed with water (2×150 mL), dried over Na2SO4, and concentrated to afford the title compound as a tan solid (4.1 g, 98%). MS (ESI), (M+H)+ 181.24; 1H NMR (CDCl3) δ 8.79 (s, 1H), 7.99 (d, 1H, J=9.2), 6.45 (d, 1H, J=9.2), 3.85 (s, 3H), 3.15 (s, 6H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in EtOAc (250 mL)
  3. washwashed with water (2×150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f2203dd369c4e13892c9f58932623f0
Source dataset
uspto-grants-2010_08
Patent number
US07786122B2

Reaction notes

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