Water → 2-Hydroxy-4-iodonicotinaldehyde

HRID 1472606Notes

Reaction equation

HRID 1472606 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.O>CC#N.CCOC(C)=O>[I:1][C:2]1[CH:3]=[CH:4][NH:5][C:6](=[O:10])[C:7]=1[CH:8]=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 100383814-Iodo-2-methoxynicotinaldehyde

Product 1

HCID 184399262-Hydroxy-4-iodonicotinaldehydeYield 58.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-iodo-2-methoxynicotinaldehyde (25 g, 83 mmol) and sodium iodide (37.0 g, 249 mmol) in MeCN (500 mL) was treated drop-wise with chlorotrimethylsilane (31.4 mL, 249 mmol) over 15 minutes. The reaction mixture was stirred at RT for 2 h, then to dryness. The residue was suspended in EtOAc, water, and satd. NaHCO3, the solid collected via filtration, triturated with MeCN and dried to afford 4-iodo-2-oxo-1,2-dihydropyridine-3-carbaldehyde (12 g, 51%) as a yellow solid. MS (ESI) m/z: 250.0 (M+H+).

Workup

  1. filtrationNaHCO3, the solid collected via filtration
  2. customtriturated with MeCN
  3. customdried

Sources & evidence

ORD record
ord-2225252afb194f998ebd15f1b0e3503f
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

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