Ethanol → Ethyl6-iodonicotinoate

HRID 1440499Notes

Reaction equation

HRID 1440499 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.Cl.CN(C)[CH2:14][CH2:15]CN=C=NCC.C(O)C>ClCCl.CN(C)C1C=CN=CC=1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:14][CH3:15])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 8190626-Iodopyridine-3-carboxylic acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 10891136Ethyl6-iodonicotinoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid (Compound B) in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (100%) and 1.15 g (9.4 mmol) of 4-dimethylaminopyridine. The resulting solution was then heated at 50° C. in an oil bath for 24.5 hours, concentrated in vacuo, partitioned between 200 ml of water and 250 ml of ethyl ether, and the layers were separated. The aqueous phase was washed with 2×150 ml-portions of ethyl ether. All organic phases were combined, washed with 75 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to give a yellow solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a white needles. PMR (CDCl3): d 1.41 (3H, t, J=7.1 Hz), 4.41 (2H, q, J=7.1 Hz), 7.85 (1H, d, J=8.2 Hz), 7.91 (1H, dd, J=8.2, 2.1 Hz), 8.94 (1H, d, J=2.1 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between 200 ml of water and 250 ml of ethyl ether
  3. customthe layers were separated
  4. washThe aqueous phase was washed with 2×150 ml-portions of ethyl ether
  5. washwashed with 75 ml of brine solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a yellow solid
  10. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4720485a6f224583b8f5e8436f900cca
Source dataset
uspto-grants-1996_03
Patent number
US05498795

Reaction notes

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