Water → Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate

HRID 710574Notes

Reaction equation

HRID 710574 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[C:10](Cl)=[CH:9][C:8]([Cl:12])=[N:7][CH:6]=1)[CH3:2].[CH3:14][NH2:15].O>C(#N)C>[Cl:12][C:8]1[CH:9]=[C:10]([NH:15][CH3:14])[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 20627001Ethyl 6-chloro-4-(methylamino)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Dichloronicotinic acid ethyl ester (43 g, 195 mmol) was dissolved in acetonitrile (600 mL), and cooled to 0° C., and then methylamine (125 mL of a 40% water solution, 977 mmol) was slowly added. The reaction mixture was stirred at 0° C. for 30 minutes and then allowed to warm to rt over 3 h. Solvent was removed in vacuo and the crude product was purified using silica gel chromatography (1:1 hexanes/ethyl acetate eluant). The title compound was isolated as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.66 (s, 1H), 8.12 (bs, 1H), 6.53 (s, 1H), 4.34 (q, J=7.2 Hz, 2H), 2.92 (s, 3H), 1.37 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureto warm to rt over 3 h
  2. customSolvent was removed in vacuo
  3. customthe crude product was purified

Sources & evidence

ORD record
ord-5b93a8a528ef45e080d2cadfe2658b7d
Source dataset
uspto-grants-2015_11
Patent number
US09181238B2

Reaction notes

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