Triethylamine → Methyl 2-(ethylcarbamoyl)isonicotinate

HRID 623567Notes

Reaction equation

HRID 623567 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([OH:13])=O)[CH:6]=1)=[O:4].[Cl-].[Mg+2].[Cl-].Cl.[CH2:18]([NH2:20])[CH3:19].C(N(CC)CC)C>ClCCl>[CH2:18]([NH:20][C:11]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][N:8]=1)[C:3]([O:2][CH3:1])=[O:4])=[O:13])[CH3:19]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 5360315Magnesium ChlorideHCID 133537524-(Methoxycarbonyl)pyridine-2-carboxylic acid

Product 1

HCID 67509052Methyl 2-(ethylcarbamoyl)isonicotinateYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(methoxycarbonyl)picolinic acid (1.00 g, 5.12 mmol) and magnesium chloride (312 mg, 3.28 mmol) in dichloromethane (10 mL) is stirred at room temperature for 0.5 hour. Then, ethylamine hydrochloride (627 mg, 7.69 mmol) and triethylamine (1.07 mL, 7.69 mmol) are added. After stirring at room temperature for 20 hours, the mixture is poured onto water (50 mL). The aqueous phase is extracted with EtOAc (50 mL×2). The combined organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:11:1) to give 525 mg (49% yield) of the title compound as a white solid.

Workup

  1. stirringAfter stirring at room temperature for 20 hours
  2. additionthe mixture is poured onto water (50 mL)
  3. extractionThe aqueous phase is extracted with EtOAc (50 mL×2)
  4. dry with materialThe combined organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (3:11:1)

Sources & evidence

ORD record
ord-0e999654a7c9400aa1777e5054e0caee
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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