Calcium Carbonate → 5-Iodo-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acid

HRID 2271118Notes

Reaction equation

HRID 2271118 reaction equation
[CH3:1][C:2]1[NH:8][CH:7]=[C:6]([C:9]([OH:11])=[O:10])[C:4](=[O:5])[CH:3]=1.C(=O)([O-])[O-].[Ca+2].[I:17]Cl.S(=O)(O)[O-].[Na+]>CN(C)C=O>[I:17][C:3]1[C:4](=[O:5])[C:6]([C:9]([OH:11])=[O:10])=[CH:7][NH:8][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 10112Calcium CarbonateHCID 24640Iodine chlorideHCID 107020144-Hydroxy-6-methyl-nicotinic acidHCID 23665763Sodium Bisulfite

Product 1

HCID 183300305-Iodo-6-methyl-4-oxo-1,4-dihydropyridine-3-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 6-methyl-4-(1H)-pyridone-3-carboxylic acid (prepared according to the procedure described in J. Org. Chem., 1972, 37, 1145-1148) (10.0 g, 65.4 mmol) and calcium carbonate (6.55 g, 65.4 mmol) in N,N-dimethylformamide (100 ml) was added iodine monochloride (21.2 g, 130.8 mmol) in N,N-dimethylformamide (20 ml). After 6 hours sodium bisulfite solution (30 ml) was added and the solution poured into ice water (500 ml). The precipitate was collected by filtration washing with water and methanol to give a cream coloured solid (15.7 g, 86%). 1H NMR (250 MHz, DMSO-d6) δ15.42 (1H, br s), 13.33 (1H, br s), 8.50 (1H, s), 2.60 (3H, s); MS (ES+) m/z 280 [MH]+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashing with water and methanol

Sources & evidence

ORD record
ord-20425879eb2f4266bc341fd61e0767dc
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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