Methyl 2-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)amino]-5-iodobenzoate → Methyl 6-iodo-4-oxo-1,4-dihydroquinoline-8-carboxylate

HRID 2273663Notes

Reaction equation

CC1(C)O[C:6](=[O:8])[C:5](=[CH:9][NH:10][C:11]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])C(=O)O1>C1(OC2C=CC=CC=2)C=CC=CC=1>[I:21][C:18]1[CH:19]=[C:20]2[C:11](=[C:12]([C:13]([O:15][CH3:16])=[O:14])[CH:17]=1)[NH:10][CH:9]=[CH:5][C:6]2=[O:8]

Participants

Conditions

Temperature: 250 °C

Procedure

Compound 98 (3.00 g, 6.96 mmol) was added under argon to refluxing diphenylether (20 mL). The mixture was stirred at 250° C. for 45 min. After cooling to room temperature, the crude mixture was chromatographed (SiO2). Diphenylether was first eliminated by elution with dichloromethane and the desired product was recovered using elution by gradient (CH2Cl2→CH2C2/EtOH (95/5, v/v)) to give compound 99 (2.01 g, 6.11 mmol) as a green solid. Yield 88%; Rf (SiO2, CH2Cl2/EtOH, 95/5, v/v) 0.31; mp 75-77° C.; IR (KBr) ν 1213, 1271, 1303, 1491, 1560, 1577, 1628, 1701, 3100-3300 cm−1; 1H NMR (200 MHz, CDCl3) δ 4.02 (s, 3H), 6.36 (dd, 1H, J=1.4, 7.6 Hz), 7.72 (dd, 1H, J=6.0, 7.6 Hz), 8.59 (d, 1H, J=2.2 Hz), 8.92 (d, 1H, J=2.2 Hz), 11.61 (se, 1H); ESI-MS m/z 329.7 [M+H]+.

Workup

temperatureAfter cooling to room temperature
customthe crude mixture was chromatographed (SiO2)
washDiphenylether was first eliminated by elution with dichloromethane
customthe desired product was recovered
washelution by gradient (CH2Cl2→CH2C2/EtOH (95/5

Sources & evidence

ORD record: ord-fc5ff963fb004fafb569b5ada998c17c
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09125937B2

Reaction notes

Loading…