Ethyl Acetate → 1-(3-(Diethoxyphosphoryl)propyl)-6-methoxy-2-methylquinolinium bromide

HRID 1810953Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([CH3:13])[CH:7]=[CH:6]2.[CH2:14]([O:16][P:17]([CH2:22][CH2:23][CH2:24][Br:25])(=[O:21])[O:18][CH2:19][CH3:20])[CH3:15].C(OCC)(=O)C>CN(C=O)C>[Br-:25].[CH2:19]([O:18][P:17]([CH2:22][CH2:23][CH2:24][N+:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[CH3:13])([O:16][CH2:14][CH3:15])=[O:21])[CH3:20]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-methoxy-2-methylquinoline (1.0 g, 5.8 mmol) and diethyl-(3-bromopropyl)-phosphonate (1.6 g, 6.4 mmol) was heated in a pressure tube at 140° C. for 16 hours. The mixture was allowed to cool to room temperature, and the resulting mass was dissolved in DMF (4 mL). The combined mixture was then added dropwise to ethyl acetate (40 mL). Precipitated purple solid was collected by centrifugation, washed with ethyl acetate (3×40 mL) and dried under vacuum to yield 1.7 g of Compound 13 which was then used without any further purification. The structure of Compound 13 is given below:

Workup

temperatureto cool to room temperature
customPrecipitated purple solid
customwas collected by centrifugation
washwashed with ethyl acetate (3×40 mL)
customdried under vacuum

Sources & evidence

ORD record: ord-d549b1387e9d4ce6b6702733da90e39b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362250B2

Reaction notes

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