Methyl 2-chloro-4-methylpyridine-3-carboxylate → HCID 44191036, compound

HRID 1959595Notes

Reaction equation

HRID 1959595 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[N:6][C:5]=1Cl.[C:13]([Cu])#[N:14]>CN1C(=O)CCC1.O.Cl>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[N:6][C:5]=1[C:13]#[N:14]

Participants

6

Reactant 2

HCID 17862852Methyl 2-chloro-4-methylpyridine-3-carboxylateHCID 178418546HCID 178418546, compound

Product 1

HCID 44191036HCID 44191036, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 2-chloro-4-methyl-nicotinic acid methyl ester (2.64 g, 14.3 mmol) and CuCN (6.4 g, 71 mmol) in NMP (5.3 mL) was heated to 180° C. for 30 min. The reaction mixture was then cooled to room temperature and diluted with water (80 mL). After vigorous stirring for 16 h, the suspension was centrifuged and the precipitate suspended in a solution of FeCl3.6H2O (5.8 g, 21 mmol) in aqueous HCl (4 M, 80 mL). After vigorous stirring for 1 h, the suspension was extracted with DCM (3×70 mL). The organic layer was dried over Na2SO4/Na2CO3, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with EA/DCM 1:10) to give the title compound. MS (m/z): 177.0 [M+H+].

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. stirringAfter vigorous stirring for 1 h
  3. extractionthe suspension was extracted with DCM (3×70 mL)
  4. dry with materialThe organic layer was dried over Na2SO4/Na2CO3
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (elution with EA/DCM 1:10)

Sources & evidence

ORD record
ord-6a78b9ce9b50444dbcef6d6cb0eafb9d
Source dataset
uspto-grants-2013_04
Patent number
US08410134B2

Reaction notes

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