Methyl iodide → 5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-methoxy-3-methyl-3,4-dihydroquinolin-2(1H)-one

HRID 394159Notes

Reaction equation

HRID 394159 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][C:22](=[O:38])[N:23]2[C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:37].CI.Cl[C:42]1C=CC=CC=1C1C=C(O)C=C2C=1C=CC(=O)N2C1C(Cl)=CC=CC=1Cl>C1COCC1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]2[C:19]=1[CH2:20][CH:21]([CH3:42])[C:22](=[O:38])[N:23]2[C:30]1[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=1[Cl:36]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 226479455-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-hydroxy-2(1H)-quinolinoneHCID 226481195-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Product 1

HCID 226479935-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-methoxy-3-methyl-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To 1 mL of THF at −78° C. was added 130 μL of a 1M solution of lithium bis(trimethylsilyl)amide in THF, then a solution of 50 mg of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-methoxyquinolin-2(1H)-one (INTERMEDIATE 6) in 2 mL of THF dropwise. The mixture was stirred for 30 min at −78° C.; then 57 mg of methyl iodide was added dropwise. The mixture was stirred 10 min at −78° C., then removed from the bath and allowed to warm to rt. The reaction was quenched by addition of 100 μL of MeOH, then poured into 10 mL of water and extracted with 2×10 mL of CH2Cl2. The combined organics were washed with 10 mL of brine, dried (MgSO4), and concentrated. The residue was purified by preparative thin-layer chromatography, eluting with 95:5 CH2Cl2-acetone, to yield a 1:1.5 mixture of 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-hydroxyquinolin-2(1H)-one and the title compound. Mass spectrum (ESI) 446 (M+1).

Workup

  1. stirringThe mixture was stirred 10 min at −78° C.
  2. customremoved from the bath
  3. temperatureto warm to rt
  4. customThe reaction was quenched by addition of 100 μL of MeOH
  5. additionpoured into 10 mL of water
  6. extractionextracted with 2×10 mL of CH2Cl2
  7. washThe combined organics were washed with 10 mL of brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by preparative thin-layer chromatography
  11. washeluting with 95:5 CH2Cl2-acetone
  12. customto yield

Sources & evidence

ORD record
ord-1f14c1f1114347a4b1d81e0910a75a0e
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

Loading…