1-Butanol → n-Butyl 3-methyl-1-(quinolin-5-yl)-1H-pyrazole-4-carboxylate

HRID 2298020Notes

Reaction equation

HRID 2298020 reaction equation
[C:1]([C:4]1[C:5](=[O:11])NC(=O)N[CH:9]=1)(=O)[CH3:2].Cl.Cl.[N:14]1[C:23]2[C:18](=[C:19]([NH:24][NH2:25])[CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.Cl.[OH:27]S(O)(=O)=O.[CH2:32](O)[CH2:33][CH2:34][CH3:35]>>[CH3:2][C:1]1[C:4]([C:5]([O:11][CH2:32][CH2:33][CH2:34][CH3:35])=[O:27])=[CH:9][N:24]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:18]=2[CH:17]=[CH:16][CH:15]=[N:14]3)[N:25]=1

Participants

6

Reactant 5

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 2345815-AcetyluracilHCID 123341075-Hydrazinoquinoline dihydrochloride

Product 1

HCID 22267799n-Butyl 3-methyl-1-(quinolin-5-yl)-1H-pyrazole-4-carboxylateYield 60%

Conditions

Temperature
23 °C

Procedure

A mixture of 5-acetyluracil (0.231 g, 1.5 mmol), 5-quinolinylhydrazine dihydrochloride (0.418 g, 1.8 mmol) and HCl (conc., 0.75 mL, 9 mmol) in n-butanol (15 mL) was heated at reflux for 20 h, cooled to 23° C., and concentrated in vacuo. The residue was dissolved in n-butanol (10 mL). The resulting solution was treated with H2SO4 (conc., 0.96 mL, 18 mmol), heated at reflux for 20 h, cooled to 23° C. and concentrated in vacuo. The residue was partitioned between EtOAc and NaOH (1 M). The aqueous layer was extracted three times with EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The brown solid residue was purified by flash chromatography (Flash 40S, hexanes-acetone 8:2) to afford 0.279 g (60%) of the desired product as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in n-butanol (10 mL)
  5. temperatureheated
  6. temperatureat reflux for 20 h
  7. temperaturecooled to 23° C.
  8. concentrationconcentrated in vacuo
  9. customThe residue was partitioned between EtOAc and NaOH (1 M)
  10. extractionThe aqueous layer was extracted three times with EtOAc
  11. dry with materialThe combined organic extracts were dried over Na2SO4
  12. concentrationconcentrated in vacuo
  13. customThe brown solid residue was purified by flash chromatography (Flash 40S, hexanes-acetone 8:2)

Sources & evidence

ORD record
ord-5597ef102931449e9059a3b6d473b501
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Reaction notes

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