Water → HCID 60631682, compound

HRID 1896014Notes

Reaction equation

HRID 1896014 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)CCC>[N+:8]([C:7]1[C:2]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15291Ethyl isonicotinateHCID 796132-Chloro-3-nitropyridine

Product 1

HCID 60631682HCID 60631682, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-chloro-3-nitropyridine (1 g, 6.31 mmol), ethyl 4-pyridinecarboxylate (1.19 g, 7.57 mmol) and potassium carbonate (1.31 g, 9.47 mmol) in n-butanol (25 mL) was stirred at reflux for 2 hours, cooled to r.t., poured into water and extracted with diethyl ether. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether 2:8) affording the title product (1.38 g).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionextracted with diethyl ether
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by flash chromatography (EtOAc—Petroleum Ether 2:8)

Sources & evidence

ORD record
ord-4e7abe765fcc4c4f8c442198e4f3898a
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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