Methyl iodide → 6-Bromo-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

HRID 44173

Reaction equation

HRID 44173 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH3:13]C([O-])(C)C.[K+].CI>CN(C=O)C.Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:13])[C:7](=[O:12])[CH2:6][CH2:5]2

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 631061416-Bromo-1-methyl-1,2,3,4-tetrahydroquinolin-2-oneYield 78%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 6-bromo-3,4-dihydro-1H-quinolin-2-one (339 mg, 1.50 mmol) in 15 ml dry DMF was added potassium tert-butylate (336 mg, 3.0 mmol). After the mixture was stirred for 30 min at room temperature, a solution of methyl iodide (426 mg, 3.0 mmol) in 5 ml dry DMF was added. Following overnight stirring, the mixture was diluted with 100 ml 1 N HCl. Extraction with ethyl acetate (2×100 mL) followed by washing of the organic extracts with water and brine, drying over MgSO4 and removal of the solvent in vacuo gave a light yellow solid. Purification by flash chromatography (hexanes/ethyl acetate, 7/3, Rf=0.21) gave 6-bromo-1-methyl-3,4-dihydro-1H-quinolin-2-one (281 mg, 1.17 mmol, 78%) as colorless needles.

Workup

  1. waitFollowing overnight
  2. stirringstirring
  3. extractionExtraction with ethyl acetate (2×100 mL)
  4. washby washing of the organic extracts with water and brine
  5. dry with materialdrying over MgSO4 and removal of the solvent in vacuo
  6. customgave a light yellow solid
  7. customPurification by flash chromatography (hexanes/ethyl acetate, 7/3, Rf=0.21)

Sources & evidence

ORD record
ord-e20cbb289c6144fe82b0f57c0a437507
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

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