Pyridine → HCID 5281089, compound

HRID 2083393Notes

Reaction equation

HRID 2083393 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)=O.Cl.Cl.[NH2:21][O:22][CH2:23][CH2:24][NH2:25].N1C=CC=CC=1.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36]>C(O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]\[C:35]([OH:37])=[O:36].[NH2:25][CH2:24][CH2:23][O:22][N:21]=[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

6

Reactant 4

HCID 1049PyridineHCID 444266Maleic AcidHCID 527103FluvoxketoneHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

Product 1

HCID 5281089HCID 5281089, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

20.4 Mmol (5.3 g) of 5-methoxy-4'-trifluoromethylvalerophenone (melting point 43°-44° C), 20.5 mmol (3.1 g) of 2-aminooxyethylaminedihydrochloride and 10 ml of pyridine were refluxed for 15 hours in 20 ml of absolute ethanol. After evaporating the pyridine and the ethanol in vacuo, the residue was dissolved in water. This solution was washed with petroleum ether and 10 ml of 50% sodium hydroxide solution were then added. Then three extractions with 40 ml of ether were carried out. The ether extract was washed successively with 20 ml of 5% sodium bicarbonate solution and 20 ml of water. After drying on sodium sulphate, the ether layer was evaporated in vacuo. Toluene was then evaporated another three times (to remove the pyridine) and the oil thus obtained was dissolved in 15 ml of absolute ethanol. An equimolar quantity of maleic acid was added to said solution and the solution was then heated until a clear solution was obtained. The ethanol was then removed in vacuo and the residue was crystallized from 10 ml of acetonitrile at +5° C. After sucking off and washing with cold acetonitrile, it was dried in air. The melting point of the resulting title compound was 120°-121.5° C.

Workup

  1. customAfter evaporating the pyridine
  2. dissolutionthe ethanol in vacuo, the residue was dissolved in water
  3. washThis solution was washed with petroleum ether and 10 ml of 50% sodium hydroxide solution
  4. additionwere then added
  5. extractionThen three extractions with 40 ml of ether
  6. extractionThe ether extract
  7. washwas washed successively with 20 ml of 5% sodium bicarbonate solution and 20 ml of water
  8. customAfter drying on sodium sulphate
  9. customthe ether layer was evaporated in vacuo
  10. customToluene was then evaporated another three times (
  11. customto remove the pyridine) and the oil
  12. customthus obtained
  13. temperaturethe solution was then heated until a clear solution
  14. customwas obtained
  15. customThe ethanol was then removed in vacuo
  16. customthe residue was crystallized from 10 ml of acetonitrile at +5° C
  17. washwashing with cold acetonitrile, it
  18. customwas dried in air
  19. customwas 120°-121.5° C.

Sources & evidence

ORD record
ord-b357d857f65346c3b1ea68f3e7c33a90
Source dataset
uspto-grants-1978_04
Patent number
US04085225

Reaction notes

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