Dimethylamine → HCID 59807121, compound

HRID 1922361Notes

Reaction equation

Cl[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:6]1=[O:27].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH3:36][NH:37][CH3:38]>C(#N)C.C1COCC1>[CH3:36][N:37]([CH3:38])[CH2:2][CH2:3][CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=2)[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:6]1=[O:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 3-(3-chloropropyl)-1-(4-methoxybenzyl)-6-nitro-3,4-dihydroquinolin-2(1H)-one (120 mg, 0.31 mmol), sodium iodide (47 mg, 0.31 mmol) and potassium carbonate in 3 mL acetonitrile was treated with dimethylamine in THF (0.3 mL of a 2M solution, 0.62 mmol). The mixture was heated at 80° C. in a sealed tube for 22 hours. The reaction was cooled to room temperature then filtered through a pad of celite. The filter pad was rinsed with methanol and the filtrate was concentrated to give a brown residue which was used without further purification. Yield: 115 mg (93.5%). 1H-NMR (CDCl3) δ: 8.07 (d, J=2.4 Hz, 1H), 8.00 (dd, J=2.7, 9 Hz, 1H), 7.11-7.08 (m, 2H), 6.98 (d, J=9.0 Hz, 1H), 6.87-6.84 (m, 2H), 5.15 (dd, J=4.2, 20.4 Hz, 2H), 3.76 (s, 3H), 3.15 (dd, J=5.4, 15.6 Hz, 1H), 2.95-2.87 (m, 4H), 2.48 (s, 6H), 1.92-1.61 (m, 4H).

Workup

temperatureThe reaction was cooled to room temperature
filtrationthen filtered through a pad of celite
washThe filter pad was rinsed with methanol
concentrationthe filtrate was concentrated
customto give a brown residue which
customwas used without further purification

Sources & evidence

ORD record: ord-ff79648ccbfa4fd4b80dc24abd1bf224
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173813B2

Reaction notes

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