Ethanol → Ethyl6-iodonicotinoate

HRID 129605

Reaction equation

HRID 129605 reaction equation
Cl.CN(C)[CH2:4][CH2:5]CN=C=NCC.[I:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][N:15]=1.C(O)C.CCOCC>C(Cl)Cl.CN(C)C1C=CN=CC=1.O>[I:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([O:20][CH2:4][CH3:5])=[O:19])=[CH:16][N:15]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 3283Diethyl EtherHCID 8190626-Iodopyridine-3-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10891136Ethyl6-iodonicotinoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of 16.230 g (84.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 90 ml of methylene chloride was cannulated into a mixture of 17.80 g (71.2 mmol) of 6-iodo-nicotinic acid in 30 ml of methylene chloride. The resulting mixture was stirred and 7.85 g (0.171 mmol) of ethanol, and then 0.826 g (6.8 mmol) of 4-dimethylaminopyridine was added and the resulting mixture refluxed at 55° C. for 20 hours and then stirred at room temperature for 12 hours. Ether and water were added and the layers separated. The aqueous layer was extracted with 2×40 ml of ether and the organic portions combined, washed with saturated NaCl, dried over Na2SO4, and concentrated yielding a white solid which was purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes) to give the title compound as a white solid.

Workup

  1. stirringstirred at room temperature for 12 hours
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with 2×40 ml of ether
  4. washwashed with saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customyielding a white solid which
  8. customwas purified by flash chromatography (SiO2, 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3032fccfcfdf489bb623754cf0a71015
Source dataset
uspto-grants-1995_11
Patent number
US05468879

Linked notes

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