Methyl iodide → HCID 59377425, compound

HRID 386651Notes

Reaction equation

HRID 386651 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[Br:13].[CH3:14][Si]([N-][Si](C)(C)C)(C)C.[K+].CI>C1COCC1>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[N:9]2[CH3:14])=[CH:4][C:3]=1[Br:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 509896411232685-09-4

Product 1

HCID 59377425HCID 59377425, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Amino-6-bromo-3,4-dihydro-1H-quinolin-2-one 280 mg (1.16 mmol) was dissolved in 8 ml THF and cooled to 0° C. KHMDS (2.56 ml, 1.27 mmol, 0.5 M in toluene) was then added dropwise, followed by dropwise addition of 80 ml (1.27 mmol) CH3I. The mixture was stirred for 12 hours, then partitioned between ethyl acetate and brine. The organic layer was dried over MgSO4 filtered and concentrated under reduced pressure. Purification by column chromatography, eluting with 75% ethyl acetate/hexanes, provided 265 mg of 7-amino-6-bromo-1-methyl-3,4-dihydro-1H-quinolin-2-one.

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography
  6. washeluting with 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b89102b215734b0ea78502dcf626a2e4
Source dataset
uspto-grants-2013_02
Patent number
US08372865B2

Reaction notes

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