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

HRID 446045

Reaction equation

HRID 446045 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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 706486-MethoxyquinaldineHCID 283500Diethyl (3-bromopropyl)phosphonate

Product 1

HCID 866399741-(3-(Diethoxyphosphoryl)propyl)-6-methoxy-2-methylquinolinium bromideYield 67.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

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

Sources & evidence

ORD record
ord-4b005a1688a141d0ad44724d369ee2cb
Source dataset
uspto-grants-2013_07
Patent number
US08476443B2

Linked notes

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