Water → 3'-Nitro-3,6-dihydro-2H-1,2'-bipyridine-4-carboxylic acid

HRID 1896018Notes

Reaction equation

HRID 1896018 reaction equation
[CH2:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH2:4][NH:3][CH2:2]1.Cl.Cl[C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[K+].[K+].O>C(O)=O>[N+:18]([C:17]1[C:12]([N:3]2[CH2:2][CH:1]=[C:6]([C:7]([OH:9])=[O:8])[CH2:5][CH2:4]2)=[N:13][CH:14]=[CH:15][CH:16]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 155107Isoguvacine Hydrochloride

Product 1

HCID 583194953'-Nitro-3,6-dihydro-2H-1,2'-bipyridine-4-carboxylic acidYield 43.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A well homogenised mixture of isoguvacine hydrochloride (497 mg, 3.04 mmol), 2-chloro-3-nitro-pyridine (482 mg, 3.04 mmol) and potassium carbonate (882 mg, 6.38 mmol), was stirred at 60° C. for 1.5 h. The reaction mixture was cooled, poured into a solution of water and formic acid (pH=3) and extracted with dichloromethane. 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-Acetic Acid 20:80:0.05) affording the title product (332 mg).

Workup

  1. stirringwas stirred at 60° C. for 1.5 h
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with brine
  5. customdried on Na2SO4
  6. customevaporated to dryness in vacuo
  7. customto afford a residue, which
  8. customwas purified by flash chromatography (EtOAc—Petroleum Ether-Acetic Acid 20:80:0.05)

Sources & evidence

ORD record
ord-31cd3288dcc1486093a8363980de89d9
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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