Formaldehyde → HCID 178519814, compound

HRID 325632Notes

Reaction equation

HRID 325632 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[OH-:13].[Na+].[CH2:15]=O>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:12])=[C:7]([CH2:15][OH:13])[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 712Formaldehyde2×HCID 14798Sodium HydroxideHCID 178516440HCID 178516440, compound

Product 1

HCID 178519814HCID 178519814, compound

Procedure

A mixture of 7-fluoro-4-hydroxyquinoline (91.5 g., containing some 5-fluoro isomer), aqueous sodium hydroxide (1.0 N, 666 ml.) and aqueous formaldehyde (37%, 91.5 ml.) was stirred at 35°-37° for 5.5 hours. A further portion of aqueous formaldehyde (37%, 91.5 ml.) was added and stirring continued for 64 hours. The solid product was collected by filtration, added to water (600 ml.) and the mixture acidified to pH 4.0 with concentrated hydrochloric acid. The solid residue was collected, washed with water and dried to give the novel 7-fluoro-4-hydroxy-3-hydroxymethylquinoline, m.p. 295-300 (containing some 5-fluoro isomer). Further product m.p. 295°-300°, was obtained from the alkaline filtrate of the reaction mixture by acidification to pH 4.0 with concentrated hydrochloric acid, and was combined with the first product.

Workup

  1. stirringstirring
  2. waitcontinued for 64 hours
  3. filtrationThe solid product was collected by filtration
  4. additionadded to water (600 ml.)
  5. customThe solid residue was collected
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-92e674c5fa5e44088cd214dbe65b896b
Source dataset
uspto-grants-1984_04
Patent number
US04442109

Reaction notes

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