Ethyl Acetate → HCID 15224422, compound

HRID 991902Notes

Reaction equation

[CH3:1][CH:2]([CH3:18])[CH2:3][NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[N+:15]([O-])=O.S([O-])([O-])(=O)=O.[Mg+2].[H][H].[C:27]([O:30][CH2:31][CH3:32])(=O)[CH3:28]>[Pt]>[CH2:27]([O:30][CH2:31][C:32]1[N:4]([CH2:3][CH:2]([CH3:18])[CH3:1])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:28]

Participants

Conditions

Temperature: 130 °C

Procedure

4-(2-Methylpropylamino)-3-nitroquinoline (30.5 g; 0.12 mol) was added to a mixture of ethyl acetate (800 mL), 5% platinum on carbon (1.5 g) and magnesium sulfate (10 g). The mixture was hydrogenated on a Parr apparatus at an initial hydrogen pressure of 30 psi. When the hydrogenation was complete, the solids were removed and the ethyl acetate was evaporated. The resulting intermediate diamine was mixed with ethoxyacetic acid (80.5 mL) and heated with stirring at 130° C. for 2-3 hours. The reaction mixture was cooled, poured into 400 mL of water and then made basic with 6N sodium hydroxide. A green solid was collected and dried to provide 8.8 g of the desired product. The structure was confirmed by nuclear magnetic resonance spectroscopy. The filtrate was extracted with ether (4×150 mL). The ether extracts were combined then evaporated to provide 11.2 g of a green solid. The solids were combined and used in subsequent reactions.

Workup

customthe solids were removed
customthe ethyl acetate was evaporated
additionThe resulting intermediate diamine was mixed with ethoxyacetic acid (80.5 mL)
temperatureheated
temperatureThe reaction mixture was cooled
additionpoured into 400 mL of water
customA green solid was collected
customdried

Sources & evidence

ORD record: ord-c4c15110f8024d6a9218a246837f1e7c
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465654B2

Reaction notes

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