Formaldehyde → HCID 178519809, compound

HRID 543679Notes

Reaction equation

HRID 543679 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[OH:12].[CH2:13]=[O:14]>[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:13][OH:14])=[C:5]2[OH:12]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 178516423HCID 178516423, compound

Product 1

HCID 178519809HCID 178519809, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

6-Fluoro-4-hydroxyquinoline was reacted with 40% aqueous formaldehyde in aqueous sodium hydroxide solution to give the novel 6-fluoro-4-hydroxy-3-hydroxymethylquinoline m.p. 310°-315°. The product was methylated with dimethyl sulphate to give the novel 6-fluoro-1-methyl-3-hydroxymethyl-4-quinolone, m.p. 209°-212°. Reaction of this product with thionyl chloride, then sodium methanethiolate gave the novel 6-fluoro-1-methyl-3-methylthiomethyl-4-quinolone, m.p. 114°-116° (from industrial methylated spirit).

Sources & evidence

ORD record
ord-84842544e08d4ba2ae2d385a9695036e
Source dataset
uspto-grants-1984_05
Patent number
US04447435

Reaction notes

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