Dimethyl Sulfate → HCID 12807883, compound

HRID 325629Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:14])=[C:7]([CH2:12][OH:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1.S(OC)(O[CH3:19])(=O)=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[C:7]([CH2:12][OH:13])=[CH:8][N:9]2[CH3:19])=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6497Dimethyl Sulfate

HCID 178519812HCID 178519812, compound

Product 1

HCID 12807883HCID 12807883, compound

Procedure

In a similar manner to that described in Example 3 7-chloro-4-hydroxy-3-hydroxymethylquinoline was treated with dimethyl sulphate to give the novel 7-chloro-1-methyl-3-hydroxymethyl-4-quinolone, m.p. 204°-206° (from industrial methylated spirit). Reaction of this product with thionyl chloride gave 7-chloro-3-chloromethyl-1-methyl-4-quinolone hydrochloride, m.p. 205°-207°, which was reacted with sodium methanethiolate to give the novel 7-chloro-1-methyl-3-methylthiomethyl-4-quinolone, m.p. 163°-164° (from industrial methylated spirit).

Sources & evidence

ORD record: ord-4e25b28e2e824817951fc2b788d54468
Source dataset: uspto-grants-1984_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04442109

Reaction notes

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