Sodium Iodide → HCID 13689097, compound

HRID 364179Notes

Reaction equation

HRID 364179 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[I-].[Na+].Cl[C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[N+:26]([O-:28])=[O:27]>CN(C)C=O.[Cu]I.[Cu].CO>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[C:19]([CH:24]=1)[O:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 118992,4-DichloronitrobenzeneHCID 24758Sodium hydrideHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 13689097HCID 13689097, compound

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a stirred solution of 15 g of methyl 2-hydroxy-4-methoxy-benzoate in 185 ml of dimethylformamide under argon was added 3.63 g of a 60% dispersion of sodium hydride in oil. To this slurry was added 12.35 g of sodium iodide, 15.69 g of copper(I)-iodide, and 0.525 g of copper powder. The mixture was heated for 15 minutes at 85° C. and 17.4 g of 2,4-dichloronitrobenzene was added. After 48 hours at 85° C., the reaction was cooled to 25° C. and methanol was added. The reaction was filtered and the filtrate was concentrated in vacuo to about 50 ml then diluted with 150 ml of ethylacetate. The solution was washed with a 20% aqueous solution of sodium thiosulfate and the organic portion was separated and dried over sodium sulfate. The solvent was evaporated to leave a tan solid. Recrystallization from ethyl acetate gave the title compound, mp 121°-123° C.

Workup

  1. temperaturethe reaction was cooled to 25° C.
  2. filtrationThe reaction was filtered
  3. concentrationthe filtrate was concentrated in vacuo to about 50 ml
  4. additionthen diluted with 150 ml of ethylacetate
  5. washThe solution was washed with a 20% aqueous solution of sodium thiosulfate
  6. customthe organic portion was separated
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated
  9. customto leave a tan solid
  10. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-cfc0a17c554a48ea833aca5b61d16ea6
Source dataset
uspto-grants-1986_08
Patent number
US04604390

Reaction notes

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