Hydrazine hydrate (1:1) → HCID 13519485, compound

HRID 1905720Notes

Reaction equation

HRID 1905720 reaction equation
[OH2:1].NN.[C:4]1(=O)[N:8]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][CH2:10]2)[C:7](=O)C2=CC=CC=C12>C(O)C>[NH2:8][CH2:9][CH2:10][CH2:11][O:1][C:16]1[CH:17]=[C:18]2[C:13]([CH2:12][CH2:11][CH2:10][CH:9]2[N:8]([CH3:7])[CH3:4])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2772290HCID 2772290, compound

Product 1

HCID 13519485HCID 13519485, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

85% hydrazine hydrate solution (3.2 ml) is added to a solution of the phthalimido tetrahydronaphthalene (about 15 g) obtained in the preceding step dissolved in absolute ethanol (160 ml). The stirred reaction mixture is refluxed for 3 hours, after which it is allowed to cool and the resulting precipitate removed by filtration. The clear yellow filtrate is evaporated in vacuo leaving a moist yellow solid, which is triturated in 5% aqueous HCl solution The resulting thick slurry is filtered and the clear filtrate made strongly alkaline with 50% sodium hydroxide solution, resulting in the formation of an oily precipitate. The precipitate is extracted with diethyl ether and the ether layers washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and the filtrate evaporated in vacuo, yielding 7.8 g of a light amber oil. NMR and IR analysis indicate that this oil is the desired amino product, which is used without further treatment for the next reaction step.

Workup

  1. customobtained in the preceding step
  2. customThe stirred reaction mixture
  3. temperatureis refluxed for 3 hours
  4. temperatureto cool
  5. customthe resulting precipitate removed by filtration
  6. customThe clear yellow filtrate is evaporated in vacuo
  7. customleaving a moist yellow solid, which
  8. customis triturated in 5% aqueous HCl solution The resulting thick slurry
  9. filtrationis filtered
  10. customresulting in the formation of an oily precipitate
  11. extractionThe precipitate is extracted with diethyl ether
  12. washthe ether layers washed with saturated sodium chloride solution
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-1917150395d546b693b8678fac6d9817
Source dataset
uspto-grants-1987_03
Patent number
US04647559

Reaction notes

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