Sodium Iodide → 2-Hydroxy-4-iodonicotinaldehyde

HRID 1411140Notes

Reaction equation

HRID 1411140 reaction equation
[I:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10]C)[N:5]=[CH:4][CH:3]=1.[I-].[Na+].Cl[Si](C)(C)C>CC#N>[I:1][C:2]1[CH:3]=[CH:4][NH:5][C:6](=[O:10])[C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 100383814-Iodo-2-methoxynicotinaldehyde

Product 1

HCID 184399262-Hydroxy-4-iodonicotinaldehydeYield 50.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Iodo-2-methoxynicotinaldehyde (25 g, 83 mmol, prepared according to WO95/29917) and sodium iodide (37.0 g, 249 mmol) were combined in MeCN (500 mL). Chlorotrimethylsilane (31.4 mL, 249 mmol) was added dropwise over 15 min. The reaction mixture was stirred at RT for 2 h and then concentrated under vacuum. The crude product was suspended in a mixture of EtOAc, water, and saturated aqueous NaHCO3, then filtered to give a dark brown solid. This solid was triturated with MeCN to yield 4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (12 g, yield 50.5%) as a yellow solid. MS (ESI) m/z: 250.0 (M+H+).

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe crude product was suspended in a mixture of EtOAc, water, and saturated aqueous NaHCO3
  3. filtrationfiltered
  4. customto give a dark brown solid
  5. customThis solid was triturated with MeCN

Sources & evidence

ORD record
ord-b1e035506c324a8f9d223e4ff865e272
Source dataset
uspto-grants-2014_12
Patent number
US08921565B2

Reaction notes

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