Water → HCID 22397182, compound

HRID 411204Notes

Reaction equation

HRID 411204 reaction equation
Cl[C:2]1[C:7]([C:8](=[O:17])[C:9](=[N:15][NH2:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][C:5]([I:18])=[CH:4][N:3]=1.C(=O)(O)[O-].[Na+].O.C(OCC)(=O)C>O1CCOCC1.CCCCCC>[I:18][C:5]1[CH:4]=[N:3][C:2]2[NH:16][N:15]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8](=[O:17])[C:7]=2[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178472856HCID 178472856, compound

Product 1

HCID 22397182HCID 22397182, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl 3-(2-chloro-5-iodo-3-pyridinyl)-2-hydrazono-3-oxopropanoate (Preparation 20, 1.0 g) and sodium bicarbonate (0.33 g) in 1,4-dioxane (15 mL) is heated to reflux for 24 h. The reaction mixture is cooled to room temperature and concentrated in vacuo to give a slurry which is treated with water (ca. 1 mL), ethyl acetate (ca. 3 mL), and hexane (ca. 2 mL). The mixture is filtered and the solid is washed with aq. ethanol (2 mL) to give, from several crops, a total of 0.48 g (54% yield) of the title compound. Physical characteristics: mp 238-242° C.; 1H NMR (300 MHz, DMSO-d6) δ 1.30, 4.23, 8.73, 8.93; IR (drift) 1675, 1561, 1526, 1468, 1390, 1374, 1339, 1313, 1304, 1249, 1209, 1158, 1141, 826, 601 cm−1; MS (ESI−) m/z 344 (M−H)−; HRMS (FAB) m/z 345.9692 (C10H8IN3O3+H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 24 h
  3. concentrationconcentrated in vacuo
  4. customto give a slurry which
  5. filtrationThe mixture is filtered
  6. washthe solid is washed with aq. ethanol (2 mL)
  7. customto give, from several crops

Sources & evidence

ORD record
ord-1bf9eb73280843848708737bda6e1dd1
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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