Isopropanol → Methyl 1,2,3,4-tetrahydroquinoline-7-carboxylate

HRID 1715846Notes

Reaction equation

C(O)(C)C.[CH3:5][O:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)=[O:8].Cl(O)(=O)(=O)=O>[Ir](Cl)Cl.CC1C(C)=C(C)C(C)=C1C.O>[CH3:5][O:6][C:7]([C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH2:15][NH:16]2)=[CH:11][CH:10]=1)=[O:8]

Participants

Conditions

Temperature: 85 °C

Procedure

1,2,3,4-Tetrahydro-quinoline-7-carboxylic acid methyl ester was obtained as follows: To a solution of his (pentamethyl-cyclopentadiene iridium dichloride) (32 mg, 0.02 equiv.) in a degassed mixture of isopropanol (9.5 ml) and water (0.5 ml) was added quinoline-7-carboxylic acid methyl ester (374 mg, 2.00 mmol) and perchloric acid (70% in water, 0.02 ml, 0.1 equiv.). The mixture was stirred at 85° C. for 17 hours, then the solvents were evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), yielding 1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester as a white solid, 305 mg (80%). MS (ISP): m/e=192.4 (M+H+); δII (300 MHz; CDCl3) 7.23 (1H, d), 7.13 (1H, s), 6.98 (1H, d), 3.86 (3H, s), 2.52 (2H, m), 3.32 (2H, t), 2.79 (2H, t), 1.94 (2H, m).

Workup

customthe solvents were evaporated
customThe residue was purified by flash chromatography (heptane/ethyl acetate gradient)

Sources & evidence

ORD record: ord-177459e003c94dcf927a3bb83fae874d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07799933B2

Reaction notes

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