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

HRID 576893Notes

Reaction equation

HRID 576893 reaction equation
[CH3:1][NH2:2].O.Cl[C:5]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=[C:7]([Cl:15])[CH:6]=1>CC#N>[Cl:15][C:7]1[CH:6]=[C:5]([NH:2][CH3:1])[C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 2764083Methyl4,6-dichloronicotinate

Product 1

HCID 71512051Methyl 6-chloro-4-(methylamino)pyridine-3-carboxylateYield 71.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

40% Methylamine in water (0.847 mL, 9.78 mmol) was added slowly over 5 minutes at 0° C. to a solution of methyl 4,6-dichloronicotinate (0.40 g, 1.94 mmol) in MeCN (6 mL). The solution was stirred at 0° C. for 30 minutes then at room temperature for 2 hours. The reaction mixture was concentrated in vacuo onto silica gel. Gradient chromatography, eluting with 5% EtOAc:c-Hex over 5 column volume and 5-50% over 15 column volume, gave methyl 6-chloro-4-(methylamino)nicotinate (278 mg, 1.386 mmol, 71.4% yield) as a white solid.

Workup

  1. waitat room temperature for 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo onto silica gel
  3. washGradient chromatography, eluting with 5% EtOAc

Sources & evidence

ORD record
ord-64a7f1a110a040c8aa342bef886c46fd
Source dataset
uspto-grants-2015_05
Patent number
US09040540B2

Reaction notes

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