Dimethylformamide → Methyl 2-Chloro-5-iodonicotinate

HRID 1199807Notes

Reaction equation

HRID 1199807 reaction equation
CN(C)C=O.P(Cl)(Cl)([Cl:8])=O.[I:11][C:12]1[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH2:15][NH:16][CH:17]=1>C(Cl)Cl>[Cl:8][C:15]1[C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:13][C:12]([I:11])=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 20073492Methyl 5-iodo-1,2-dihydro-3-pyridinecarboxylate

Product 1

HCID 2764559Methyl 2-Chloro-5-iodonicotinateYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 0.12 ml of dry dimethylformamide and 0.14 ml of distilled phosphorus oxychloride in 20 ml of anhydrous methylene chloride are added 0.28 g of methyl 5-iodo-1,2-dihydro-3-pyridinecarboxylate in one portion. The mixture is stirred at room temperature under a nitrogen atmosphere for 28 hours. Workup as described in Procedure 1 yields 0.13 g (43%) of recrystallized methyl 2-chloro-5-iodo-3-pyridinecarboxylate.

Sources & evidence

ORD record
ord-da0fe0c031234f0899e7810d816d2956
Source dataset
uspto-grants-1990_02
Patent number
US04902796

Reaction notes

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