Dimethyl Sulfoxide → (3,7-Dichloroquinolin-8-yl)methyl nonanoate

HRID 1248073Notes

Reaction equation

HRID 1248073 reaction equation
[CH2:1]([C:10]([OH:12])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]C.C[O-].[Na+].CS(C)=O.[Cl:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[C:26]([Cl:31])[C:25]=2[CH2:32]Cl>O>[Cl:20][C:21]1[CH:22]=[N:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[C:26]([Cl:31])[C:25]=2[CH2:32][O:12][C:10]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 2969Decanoic AcidHCID 10942334Sodium MethoxideHCID 13090784HCID 13090784, compound

Product 1

HCID 13264094(3,7-Dichloroquinolin-8-yl)methyl nonanoateYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

16 parts by weight of nonanecarboxylic acid, 20 parts by weight of 30% strength sodium methylate solution and 440 parts by weight of dimethylsulfoxide are stirred for 1 hour at 100° C. Thereafter, 24.5 parts by weight of 3,7-dichloro-8-chloromethylquinoline are introduced and the reaction mixture is stirred for a further 2 hours at 100° C. The reaction solution is then cooled, water is added and the precipitated solid is filtered off under suction and recrystallized from toluene. 32.5 parts by weight (89% of theory) of 3,7-dichloro-8-octylcarbonyloxymethylquinoline of melting point 92° C. are obtained.

Workup

  1. temperatureThe reaction solution is then cooled
  2. filtrationthe precipitated solid is filtered off under suction
  3. customrecrystallized from toluene

Sources & evidence

ORD record
ord-ef45b2c9841048f981eca4095ac307f5
Source dataset
uspto-grants-1985_06
Patent number
US04522646

Reaction notes

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