Sodium Iodide → HCID 68621373, compound

HRID 340449Notes

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

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

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

Sources & evidence

ORD record: ord-1035dad3a08b4a62a64fb1fcb57e6477
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895585B2

Reaction notes

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