Potassium Iodide → HCID 53392258, compound

HRID 1922484Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:18].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:28][NH:29][CH3:30]>C(#N)C.O>[CH3:28][N:29]([CH3:30])[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of 1-(3-chloropropyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (5.22 g, 19.43 mmol), potassium iodide (3.22 g, 19.43 mmol) and potassium carbonate (16.11 g, 117 mmol) in acetonitrile (100 ml) was added dimethylamine hydrochloride (6.34 g, 78 mmol). The resulting mixture was stirred overnight at 50° C. The mixture was then cooled to room temperature, diluted with water and extracted with dichloromethane (3×). The combined organics were dried, filtered and concentrated, then chromatographed on silica gel using 0-10% (2M NH3 in MeOH) in dichloromethane as the eluent. 1H NMR (DMSO-d6) δ 8.14-8.10 (m, 2H), 7.37 (d, J=9.6 Hz, 1H), 3.94 (t, J=7.5 Hz, 2H), 3.00 (t, J=7.5 Hz, 2H), 2.62 (t, J=7.5 Hz, 1H), 2.27 (t, J=7 Hz, 2H), 2.13 (s, 6H), 1.66 (quint, J=7.5 Hz, 1H). ESI-MS (m/z, %) 278 (MH+, 100).

Workup

temperatureThe mixture was then cooled to room temperature
extractionextracted with dichloromethane (3×)
customThe combined organics were dried
filtrationfiltered
concentrationconcentrated
customchromatographed on silica gel using 0-10% (2M NH3 in MeOH) in dichloromethane as the eluent

Sources & evidence

ORD record: ord-5bca528641b6424ea75e1fb331a24603
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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