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

HRID 378855Notes

Reaction equation

HRID 378855 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[N:10]=[CH:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][CH:6]=1)=[O:4].N1C=C(C(OC)=O)C=C[C:16]=1C(OC)=O.[Cl-].[Mg+2].[Cl-].CNC.Cl>C1COCC1.O>[CH3:1][N:2]([CH3:14])[C:3]([C:5]1[N:10]=[CH:9][C:8]([C:11]([O:13][CH3:16])=[O:12])=[CH:7][CH:6]=1)=[O:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 234911Dimethyl 2,5-pyridine dicarboxylateHCID 5360315Magnesium ChlorideHCID 216968616-Dimethylaminocarbonyl nicotinic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation of 6-[(dimethylamino)carbonyl]-3-pyridine carboxylic acid. 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-4e67abad4a58427c892f8a54200a0785
Source dataset
uspto-grants-2001_10
Patent number
US06297233B1

Reaction notes

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