Hydrochloric Acid → Methyl 6-[(dimethylamino)carbonyl]-3-pyridine carboxylate

HRID 378860Notes

Reaction equation

HRID 378860 reaction equation
[N:1]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[CH:4]=[CH:3][C:2]=1[C:11]([O:13]C)=O.[Cl-].[Mg+2].[Cl-].[CH3:18][NH:19][CH3:20].Cl>C1COCC1.O>[CH3:18][N:19]([CH3:20])[C:11]([C:2]1[N:1]=[CH:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1)=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 234911Dimethyl 2,5-pyridine dicarboxylateHCID 5360315Magnesium Chloride

Product 1

HCID 10703558Methyl 6-[(dimethylamino)carbonyl]-3-pyridine carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 2° C. slurry of dimethyl 2,5-pyridinedicarboxylate (50 g, 0.256 mol) in THF (700 mL) was added magnesium chloride (26.8 g, 0.282 mol). After stirring for 15 min, dimethylamine (2 M in THF, 256 mL, 0.512 mol) was added dropwise over 40 min. The mixture was stirred for 30 min at 2° C. and then at room temperature for 1 h. To the mixture was added water (100 mL) and 1 N HCl (300 mL). The mixture was extracted with ethyl acetate (4×400 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo to provide 53 g (100%) of methyl 6-[(dimethylamino)carbonyl]-3-pyridine carboxylate a pale yellow solid.

Workup

  1. stirringThe mixture was stirred for 30 min at 2° C.
  2. waitat room temperature for 1 h
  3. extractionThe mixture was extracted with ethyl acetate (4×400 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-442f77cd1b22489cb2f0f42a2eb2790a
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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