Acetohydrazide → 6-[3,5-Dimethyl-1,2,4-triazol-4-yl]-2-methoxy-8-methylquinoline

HRID 568384Notes

Reaction equation

HRID 568384 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[C:7]([NH:10][C:11]1[CH:12]=[C:13]2[C:18](=[C:19]([CH3:21])[CH:20]=1)[N:17]=[C:16]([O:22][CH3:23])[CH:15]=[CH:14]2)(=O)[CH3:8].[C:24]([NH:27][NH2:28])(=O)[CH3:25]>C1(C)C=CC=CC=1>[CH3:8][C:7]1[N:10]([C:11]2[CH:12]=[C:13]3[C:18](=[C:19]([CH3:21])[CH:20]=2)[N:17]=[C:16]([O:22][CH3:23])[CH:15]=[CH:14]3)[C:24]([CH3:25])=[N:27][N:28]=1

Participants

5

Reactant 3

HCID 14039AcetohydrazideHCID 24819Phosphorus pentachlorideHCID 198670766-Acetamido-2-methoxy-8-methylquinoline

Product 1

HCID 198670866-[3,5-Dimethyl-1,2,4-triazol-4-yl]-2-methoxy-8-methylquinolineYield 26.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus pentachloride (1.0 g) was added to a stirred solution of 6-acetamido-2-methoxy-8-methylquinoline (1.0 g) in toluene (50 cm3) and the mixture was stirred at 50° for 15 minutes. Acetyl hydrazine (1.35 g) was then added and the mixture was stirred for 3 hours at 60°. The toluene was removed in vacuo, the residue dissolved in ethanol, and aqueous ammonia solution (S.G. 0.88) (25 cm3) was added. Dichloromethane (100 cm3) was added and the organic phase was separated. The aqueous phase was further extracted with dichloromethane (2×25 cm3), and the combined organic phases were dried (MgSO4) and evaporated to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with dichloromethane:methanol, 19:1. Combination and evaporation of appropriate fractions afforded 6-[3,5-dimethyl-1,2,4-triazol-4-yl]-2-methoxy-8-methylquinoline (0.306 g), which was recrystallised from toluene to give microcrystals, m.p. 211°-213° (0.066 g).

Workup

  1. stirringthe mixture was stirred for 3 hours at 60°
  2. customThe toluene was removed in vacuo
  3. dissolutionthe residue dissolved in ethanol
  4. additionaqueous ammonia solution (S.G. 0.88) (25 cm3) was added
  5. additionDichloromethane (100 cm3) was added
  6. customthe organic phase was separated
  7. extractionThe aqueous phase was further extracted with dichloromethane (2×25 cm3)
  8. dry with materialthe combined organic phases were dried (MgSO4)
  9. customevaporated
  10. customto give a solid which
  11. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  12. washeluting with dichloromethane
  13. customCombination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-6157bc9009e44c0e9aecb012633c3267
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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