Sodium Carbonate → 6-[3,5-dimethyl-1,2,4-triazol-4-yl]-8-methyl-2-(1H)-quinolone

HRID 568366Notes

Reaction equation

HRID 568366 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=2)[N:13]=[C:12]([O:18]C)[CH:11]=[CH:10]3)[C:5]([CH3:20])=[N:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[CH3:20][C:5]1[N:6]([C:7]2[CH:8]=[C:9]3[C:14](=[C:15]([CH3:17])[CH:16]=2)[NH:13][C:12](=[O:18])[CH:11]=[CH:10]3)[C:2]([CH3:1])=[N:3][N:4]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 198670866-[3,5-Dimethyl-1,2,4-triazol-4-yl]-2-methoxy-8-methylquinoline

Product 1

HCID 198670956-[3,5-dimethyl-1,2,4-triazol-4-yl]-8-methyl-2-(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of 6-[3,5-dimethyl-1,2,4-triazol-4-yl]-2-methoxy-8-methylquinoline (0.24 g) in 5M hydrochloric acid (20 cm3) was heated under reflux for 1 hour. The cooled solution was then basified to pH8 with 10% aqueous sodium carbonate solution and extracted with chloroform (5×50 cm3). The combined and dried (MgSO4) organic phases were evaporated in vacuo and the residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane:methanol, 20:1, to afford 6-[3,5-dimethyl-1,2,4-triazol-4-yl]-8-methyl-2-(1H)-quinolone, 0.66H2O, m.p. 308°-310° (0.17 g).

Workup

  1. temperatureunder reflux for 1 hour
  2. extractionextracted with chloroform (5×50 cm3)
  3. dry with materialdried (MgSO4) organic phases
  4. customwere evaporated in vacuo
  5. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-366025ba8ce0430d9bf43b40b29ebcb8
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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