Selenious Acid → (7-Chloro-2-formyl-quinolin-8-yl)-acetic acid ethyl ester

HRID 505223

Reaction equation

[Se](O)(O)=[O:2].[CH2:5]([O:7][C:8](=[O:22])[CH2:9][C:10]1[C:11]([Cl:21])=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]2)[CH3:6]>O1CCOCC1.O>[CH2:5]([O:7][C:8](=[O:22])[CH2:9][C:10]1[C:11]([Cl:21])=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH:20]=[O:2])[CH:16]=[CH:15]2)[CH3:6]

Participants

Conditions

Temperature: 100 °C

Procedure

Selenious acid (193 mg, 1.50 mmol, 1.1 equiv) was added to a solution of (7-chloro-2-methyl-quinolin-8-yl)-acetic acid ethyl ester in dioxane (12 ml). The reaction mixture was heated to 100° C. After 20 and 40 minutes, additional portions of selenious acid (88 mg each) were added, and heating was continued for a total of 90 minutes. After cooling, the reaction mixture was diluted with water, filtered, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20) to afford the title compound (292 mg, 77%). 1H NMR (400 MHz, CDCl3): δ=10.18 (s, 1H), 8.31 (d, J=8.1 Hz, 1H), 8.04 (d, J=8.1 Hz, 1H), 7.82 (d, J=7.7 Hz, 1H), 7.71 (d, J=7.7 Hz, 1H), 4.61 (s, 2H), 4.22 (q, J=7.3 Hz, 2H), 1.28 (t, J=7.3 Hz, 3H). MS (ES+): 278.2 (M+H)+.

Workup

temperatureheating
customwas continued for a total of 90 minutes
temperatureAfter cooling
filtrationfiltered
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20)

Sources & evidence

ORD record: ord-3b03c3282f3e49b7a222d2843d5dbf6b
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07781438B2

Linked notes

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