Lithium iodide → HCID 23031144, compound

HRID 1766669Notes

Reaction equation

HRID 1766669 reaction equation
[CH:1]1([NH:7][C:8](=[O:31])[C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]4[C:17]=3[CH2:18][CH2:19][CH2:20]4)[CH:12]=[CH:11][C:10]=2[O:29]C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[I-].[Li+]>N1C(C)=CC(C)=CC=1C>[CH:1]1([NH:7][C:8](=[O:31])[C:9]2[CH:14]=[C:13]([O:15][C:16]3[C:24]([CH3:25])=[CH:23][C:22]([N+:26]([O-:28])=[O:27])=[C:21]4[C:17]=3[CH2:18][CH2:19][CH2:20]4)[CH:12]=[CH:11][C:10]=2[OH:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 66321Lithium iodideHCID 23031268HCID 23031268, compound

Product 1

HCID 23031144HCID 23031144, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

N-Cyclohexyl-2-methoxy-5-(5-methyl-7-nitroindan-4-yl oxy)benzamide (40 mg) and lithium iodide (38 mg) were dissolved in 2,4,6-collidine (2 mL). The mixture was heated under reflux for 15 hours. Adding water, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1) to give the title compound (28 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 hours
  3. extractionAdding water, the reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1 mol/L hydrochloric acid, water and brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-0500a0fd2af647638fd8cc21fe8754d9
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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