6-Iodopyridine-3-carboxylic acid → Ethyl6-iodonicotinoate

HRID 2258080Notes

Reaction equation

HRID 2258080 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1.[I:13]C1C=CC(C(O)=O)=CN=1.C(C(CC)(CC)C([O-])([O-])[O-])C>>[I:13][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 8190626-Iodopyridine-3-carboxylic acidHCID 2799611Ethyl 6-chloronicotinateHCID 21875354Triethylorthoaceate

Product 1

HCID 10891136Ethyl6-iodonicotinoateYield 92.4%

Procedure

Using the same procedure for ethyl 6-chloronicotinate but instead using 6-iodonicotinic acid (7.14 g, 28.67 mmol) and triethylorthoacetate (13.96 g, 86.02 mmol) gave the titled compound as a white solid (7.340 g, 26.49 mmol, 92.4%).

Sources & evidence

ORD record
ord-9ee0f62c925f46d19306e35bb46e2deb
Source dataset
uspto-grants-1997_08
Patent number
US05659042

Reaction notes

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