Methyl iodide → HCID 9855627, compound

HRID 993147Notes

Reaction equation

HRID 993147 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:7][C:6](=[O:12])[CH:5]=[CH:4][C:3]1=2.[CH3:13]I>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]2[C:2](=[O:1])[CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 2674502-Hydroxy-7,8-dihydro-5(6H)-quinolinone

Product 1

HCID 9855627HCID 9855627, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of compound 5 (8.2 g, 50 mmol) prepared as described in Example 1, methyl iodide (15.7 mL, 250 mmol), and silver carbonate (8.3 g, 30 mmol) in 150 mL of chloroform was stirred in a flask at room temperature for 48 hours. The reaction mixture was filtered through celite, and the filtrate was concentrated in vacuo, and purified by column chromatography (elution with hexanes-ethyl acetate 3:1) to give compound 8 (7.2 g, 81%) as a light yellow solid, mp 101-102° C. 1H NMR (CDCl3): δ 2.15 (quin, J=6.4 Hz, 2H), 2.62 (t, J=6.6 Hz, 2H), 3.01 (t, J=6.2 Hz, 2H), 3.99 (s, 3H), 6.65 (d, J=8.7 Hz, 1H), 8.15 (d, J=8.7 Hz, 1H); 13C NMR (CDCl3): δ 22.01, 32.49, 38.20, 53.89, 109.83, 122.73, 137.62, 163.89, 166.11, 197.08. FABMS: m/e 178 (M+1, 100), 154 (16), 137 (16). Analysis: Calcd. for C10H11NO2: C, 67.78; H, 6.26; N, 7.90. Found: C, 67.94; H, 6.36; N, 7.91.

Workup

  1. customprepared
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified by column chromatography (elution with hexanes-ethyl acetate 3:1)

Sources & evidence

ORD record
ord-68cbfcf408fa4d749d8c2f8b55d9d5de
Source dataset
uspto-grants-2002_10
Patent number
US06472408B1

Reaction notes

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