Pyridine → HCID 88780851, compound

HRID 1701359Notes

Reaction equation

HRID 1701359 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]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=O.[ClH:18].Cl.[O:20]([CH2:22][CH2:23][NH2:24])[NH2:21].N1C=CC=CC=1>C(O)C>[ClH:18].[NH2:24][CH2:23][CH2:22][O:20][N:21]=[C:7]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 143623262-(O-aminooxy)ethylamine dihydrochlorideHCID 203478995-Methoxy-1-(4-nitrophenyl)pentan-1-one

Product 1

HCID 88780851HCID 88780851, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.35 Mmol (1.27 g) of 5-methoxy-4'-nitrovalerophenone (melting point 64.5°-65.5° C.), 5.35 mmol (0.80 g) of 2-aminoxyethylamine dihydrochloride and 0.34 ml of pyridine were refluxed for 2 hours in 5 ml of absolute ethanol. After evaporating the reaction mixture to dryness in vacuo, 25 ml of water and 10 ml of 2 N sodium hydroxide solution were added and extracted with 25 and 10 ml, respectively, of methylene chloride. The extracts were dried over sodium sulphate and then evaporated to dryness in vacuo. Toluene was added another two times to the resulting base which was evaporated in vacuo. The residue was dissolved in absolute ethanol and an equimolar quantity of alcoholic hydrochloric acid was added. After the addition of diethyl ether, the title compound crystallized. Melting point 121.5°-122.5° C.

Workup

  1. customAfter evaporating the reaction mixture to dryness in vacuo, 25 ml of water and 10 ml of 2 N sodium hydroxide solution
  2. additionwere added
  3. extractionextracted with 25 and 10 ml
  4. dry with materialThe extracts were dried over sodium sulphate
  5. customevaporated to dryness in vacuo
  6. additionToluene was added another two times to the resulting base which
  7. customwas evaporated in vacuo
  8. dissolutionThe residue was dissolved in absolute ethanol
  9. additionan equimolar quantity of alcoholic hydrochloric acid was added
  10. additionAfter the addition of diethyl ether
  11. customthe title compound crystallized

Sources & evidence

ORD record
ord-99b52431bdb148ecb16f3db88c447905
Source dataset
uspto-grants-1980_03
Patent number
US04192893

Reaction notes

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