Carbon Dioxide → Methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate

반응식

[Li][C:2]1([Si](C)(C)C)C2N=CC(C)=CC=2CCC1.C(=O)=O.[CH3:20][C:21]1[CH:22]=[N:23][C:24]2[C:25]([Si](C)(C)C)([C:31]([O-:33])=[O:32])[CH2:26][CH2:27][CH2:28][C:29]=2[CH:30]=1.[Li+]>>[CH3:2][O:33][C:31]([CH:25]1[C:24]2[N:23]=[CH:22][C:21]([CH3:20])=[CH:30][C:29]=2[CH2:28][CH2:27][CH2:26]1)=[O:32]

참가 물질

반응물 3

HCID 280Carbon Dioxide

HCID 23704295HCID 23704295, 화합물

HCID 178506786HCID 178506786, 화합물

생성물 1

HCID 12278960Methyl 3-methyl-5,6,7,8-tetrahydroquinoline-8-carboxylate

실험 절차

8-Lithio-5,6,7,8-tetrahydro-3-methyl-8-trimethylsilylquinoline, prepared as in Example 3, is blown over onto ether at 0° C. through which a vigorous stream of CO2 gas is being passed. After the addition the resulting solid, lithium 5,6,7,8-tetrahydro-3-methyl-8-trimethylsilylquinoline-8-carboxylate, is removed by filtration. This is then dissolved in methanol (200 ml) and the solution treated with HCl gas to excess and heated at reflux for 4 hours. The solvent is removed in vacuo and the residue dissolved in water (50 ml), made alkaline with 2N NaOH and extracted with chloroform. The extracts are dried, evaporated and the residue distilled to give the title compound as a pale yellow oil bp 120°/0.25 mm.