Ethanol → Ethyl6-iodonicotinoate

HRID 495904Notes

Reaction equation

HRID 495904 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.[CH2:12](N=C=N)[CH3:13].C(O)C.CN(C1C=CC=CN=1)C>ClCCl>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:12][CH3:13])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 218852-DimethylaminopyridineHCID 8190626-Iodopyridine-3-carboxylic acidHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 10891136Ethyl6-iodonicotinoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 6-iodonicotinic acid (23.38 g, 94.20 mmol) in dichloromethane (100 ml) was added a solution of 13-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.86 g, 103.6 mmol) in dichloromethane (250 ml). To this mixture was added ethanol (12.40 g, 269.27 mmol) followed by dimethylaminopyridine (1.15 g, 9.41 mmol). The mixture was heated at 50° C. for 24.5 hours, concentrated in vacuo, and diluted with water (200 ml) then extracted with ethyl ether (550 ml). The combined organic phases were washed with saturated aqueous NaCl, dried (MgSO4) and concentrated to a yellow solid. Purification by flash chromatography (silica, 10% EtOAc-hexane) afforded the title compound as white needles: mp 48-49° C.; 1H NMR (CDCl3): δ 8.94 (1H, d, J=2.1 Hz), 7.91 (1H, dd, J=2.1, 8.2 Hz), 7.85 (1H, d, J=8.2 Hz), 4.41 (2H, q, J=7.1 Hz), 1.41 (3H, t, J=7.1 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water (200 ml)
  3. extractionthen extracted with ethyl ether (550 ml)
  4. washThe combined organic phases were washed with saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to a yellow solid
  7. customPurification by flash chromatography (silica, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-4fe68455c3a34677a2be40fc54f7642a
Source dataset
uspto-grants-2005_09
Patent number
US06942980B1

Reaction notes

Loading…