Formaldehyde → HCID 20158978, compound

HRID 985989Notes

Reaction equation

HRID 985989 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([C:18]2[C:19]([CH3:25])=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:17])[CH:13]=[CH:12]2.[CH2:26]=[O:27].[Cl-].[NH4+]>CCCCCC.C1COCC1>[OH:27][CH2:26][C:7]1[CH:8]=[C:9]([C:18]2[C:19]([CH3:25])=[N:20][C:21]([CH3:24])=[CH:22][CH:23]=2)[CH:10]=[C:11]2[C:16]=1[NH:15][C:14](=[O:17])[CH:13]=[CH:12]2

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 25517Ammonium ChlorideHCID 14221015HCID 14221015, compoundHCID 178418339Butyllithium

Product 1

HCID 20158978HCID 20158978, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of n-butyl lithium [1.04 cm3 of a 1.6M solution in n-hexane] was added at -70° to a stirred solution of 8-bromo-6-[2,6-dimethyl-pyrid-3-yl]-2-(1H)-quinolone (0.25 g) in THF (20 cm3) under nitrogen. After 2 hours, gaseous formaldehyde [generated by sublimation of paraformaldehyde (0.3 g)] was passed over the solution, and, after stirring for a further 10 minutes, the mixture was allowed to warm to room temperature. Saturated ammonium chloride solution (10 cm3) was then added and the mixture was extracted with chloroform (3×50 cm3). The combined and dried (MgSO4) organic extracts were evaporated and the residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane:methanol, 19:1. Combination and evaporation of the appropriate fractions afforded 8-hydroxymethyl-6-[2,6-dimethylpyrid-3-yl]-2-(1H)-quinolone. 0.1H2O, m.p. 218.5°-221° (0.094 g).

Workup

  1. extractionthe mixture was extracted with chloroform (3×50 cm3)
  2. dry with materialdried (MgSO4) organic extracts
  3. customwere evaporated
  4. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  5. washeluting with dichloromethane
  6. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-c53450e04c0540e58d7c18ce5a07c3df
Source dataset
uspto-grants-1987_12
Patent number
US04710507

Reaction notes

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