Triethylamine → HCID 57455410, compound

HRID 1623210Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19].C(N(CC)CC)C.[CH2:28]([O:30][CH:31]([O:35][CH2:36][CH3:37])[CH2:32][CH2:33][NH2:34])[CH3:29]>ClCCl.O>[CH2:28]([O:30][CH:31]([O:35][CH2:36][CH3:37])[CH2:32][CH2:33][NH:34][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[CH:10][C:9]=1[N+:18]([O-:20])=[O:19])[CH3:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium carbonate (19.9 g, 144 mmol) was added to a mixture of 4-chloro-3-nitroquinoline (30 g, 144 mmol) and dichloromethane (150 mL). The reaction mixture was sparged with nitrogen. Triethylamine (21.8 g, 216 mmol) was added dropwise. The reaction mixture was cooled to 0° C. then a solution of 3,3-diethoxypropylamine (25.4 g, 173 mmol) in dichloromethane (50 mL) was added dropwise over a period of 15 minutes. The reaction mixture was stirred at room temperature for 3 hours. Dichloromethane and water (200 mL) were added. The layers were separated. The organic layer was washed with brine (×2). The combined aqueous layers were extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to provide 45 g of N-(3,3-diethoxypropyl)-3-nitroquinolin-4-amine.

Workup

customThe reaction mixture was sparged with nitrogen
customThe layers were separated
washThe organic layer was washed with brine (×2)
extractionThe combined aqueous layers were extracted with dichloromethane
dry with materialThe combined organic layers were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c106ff70e62f4350943b09da401968bb
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778963B2

Reaction notes

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