Yield:57311-38-3 81%

Reaction Conditions:

in chloroform;

Steps:

5.a EXAMPLE 5

(a) Preparation of 5,6,7,8-Tetrahydro-2-methoxy-5-oxo-quinoline (8) (Formula II: Q=-CH₂-; -W-X-=-N=C(OR₃)-, R³=-CH₃) 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.

References:

US2002/156096,2002,A1