Hydrogen iodide → Diethyl 4-iodopyridine-2,6-dicarboxylate

HRID 1513992Notes

Reaction equation

HRID 1513992 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=1.[IH:18].C([O-])(O)=O.[Na+]>CCO>[I:18][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:5]=[C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:3]=1

Participants

5

Reactant 3

HCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 13794409Diethyl 4-bromopyridine-2,6-dicarboxylate

Product 1

HCID 14145737Diethyl 4-iodopyridine-2,6-dicarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of diethyl 4-bromopyridine-2,6-dicarboxylate (8.36 g, 27.7 mmol), 57% (w/w) aqueous hydriodic acid (31.05 g, 138.4 mmol) and EtOH (67 mL) was stirred at 50° C. for 1 h and neutralized with saturated NaHCO3 solution. The product was extracted from the aqueous phase with CH2Cl2 (2×300 mL). The combined organic fractions were dried with Na2SO4 and evaporated to dryness. Yield was 5.24 g (54%). ESI-TOF-MS [M+H]+: calc. for C11H13INO4+ 349.99. found 349.99.

Workup

  1. extractionThe product was extracted from the aqueous phase with CH2Cl2 (2×300 mL)
  2. dry with materialThe combined organic fractions were dried with Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-d270428429a54bdf9e9a48f15a283582
Source dataset
uspto-grants-2012_07
Patent number
US08221719B2

Reaction notes

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