Sodium Iodide → HCID 54141905, compound

HRID 726632Notes

Reaction equation

HRID 726632 reaction equation
Cl[C:2]1[C:11]([CH2:12][P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH3:22])=[C:7]([CH3:21])[CH:8]=2)[N:3]=1.[I-:23].[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(=O)CC.C(OCC)(=O)C>[CH2:16]([O:15][P:13]([CH2:12][C:11]1[C:2]([I:23])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH3:21])=[C:6]([CH3:22])[CH:5]=2)([O:18][CH2:19][CH3:20])=[O:14])[CH3:17]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 54299050Phosphonic acid, [(2-chloro-6,7-dimethyl-3-quinolinyl)methyl]-, diethyl ester

Product 1

HCID 54141905HCID 54141905, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Chloro-3-diethylphosphonomethyl-6,7-dimethylquinoline (0.40 g, 1.17 mmol), prepared as described in Example 4 was dissolved in 2-butanone (20 ml) and treated with sodium iodide (0.39 g, 2.6 mmol) and p-toluenesulfonic acid (0.11 g, 0.58 mmol). The mixture was refluxed for 10 hours. Ethyl acetate and saturated sodium hydrogen carbonate were added. The organic phase was separated and filtered through a pad of silica gel. Evaporation of solvents gave 0.28 g of 3-diethylphosphonomethyl-6,7-dimethyl-2-iodoquinoline.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. customThe organic phase was separated
  3. filtrationfiltered through a pad of silica gel
  4. customEvaporation of solvents

Sources & evidence

ORD record
ord-86ac58cb62634e7b8da6395d96e67a65
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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