Sodium Iodide → HCID 68621373, compound

HRID 1620056

Reaction equation

HRID 1620056 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH2:12].S(OC)(O[CH3:17])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(OCC)(=O)C.CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][CH3:17]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 151125453-Bromoquinolin-8-amine

Product 1

HCID 68621373HCID 68621373, compoundYield 21.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A DMF (2 ml) solution containing 3-bromoquinolin-8-amine (223 mg), dimethyl sulfate (189 mg), potassium carbonate (415 mg), and sodium iodide (20 mg) were added to a tube and the tube was sealed, followed by stirring at 95° C. for 17 hours. The reaction solution was cooled to room temperature, ethyl acetate was added, an insoluble precipitate was removed, and the organic layer was washed with 1M hydrochloric acid, water, and saturated saline. Subsequently, the organic layer was dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=0:1 to 1:1), and a yellow solid of 3-bromo-N-methylquinolin-8-amine (52 mg) was thus obtained.

Workup

  1. additionwere added to a tube
  2. customthe tube was sealed
  3. temperatureThe reaction solution was cooled to room temperature
  4. customan insoluble precipitate was removed
  5. washthe organic layer was washed with 1M hydrochloric acid, water, and saturated saline
  6. dry with materialSubsequently, the organic layer was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=0:1 to 1:1)

Sources & evidence

ORD record
ord-d6a98efcf77f466d877002e10124b5a4
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Linked notes

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