Dimethyl Sulfoxide → HCID 13264095, compound

HRID 1248074Notes

Reaction equation

HRID 1248074 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].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:7][C:6]([C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=1[N+:1]([O-:3])=[O:2])=[O:8]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 110872-Nitrobenzoic acidHCID 10942334Sodium MethoxideHCID 13090784HCID 13090784, compound

Product 1

HCID 13264095HCID 13264095, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

33 parts by weight of 2-nitrobenzoic acid, 40 parts by weight of 30% strength sodium methylate solution and 440 parts by weight of dimethylsulfoxide are stirred for 2 hours at 100° C. Thereafter, 49 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 solution is then cooled, water is added and the precipitated solid is filtered off under suction and recrystallized from toluene. 69 parts by weight (92% of theory) of 3,7-dichloro-8-[(2-nitrophenyl)-carbonyloxymethyl]-quinoline of melting point 152° C. are obtained.

Workup

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

Sources & evidence

ORD record
ord-ad10542a9d964f148da9ba2aefa905f2
Source dataset
uspto-grants-1985_06
Patent number
US04522646

Reaction notes

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