Hydrazine hydrate (1:1) → HCID 20265975, compound

HRID 1719866Notes

Reaction equation

HRID 1719866 reaction equation
[OH2:1].NN.[C:4]1(=O)[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:7](=O)[C:6]2=CC=CC=[C:5]12>C(O)C>[NH2:8][CH2:7][CH2:6][CH2:5][O:1][C:16]1[CH:17]=[C:18]2[C:13]([CH:12]=[CH:11][CH:10]=[C:9]2[N:8]2[CH2:4][CH2:5][CH2:6][CH2:7]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 79252N-1-Naphthylphthalimide

Product 1

HCID 20265975HCID 20265975, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

85% hydrazine hydrate (9.6 ml) is added to a stirred solution of the phthalimido naphthalene prepared as described in the previous step (about 50 g) in absolute ethanol (about 500 ml). The reaction mixture is heated at reflux for about 3 hours and allowed to cool. The resulting precipitate is removed by filtration and washed with absolute ethanol. The filtrate is evaporated in vacuo and the residue triturated with 5% aqueous hydrochloric acid. The aqueous suspension is filtered and the solid washed with 5% hydrochloric acid. The filtrate is made strongly alkaline with 50% sodium hydroxide solution, resulting in an oily precipitate which is extracted into diethyl ether. The ether extract is washed with saturated sodium chloride solution, dried, filtered and the filtrate evaporated in vacuo, yielding the desired amine as an oil.

Workup

  1. customprepared
  2. temperatureThe reaction mixture is heated
  3. temperatureat reflux for about 3 hours
  4. temperatureto cool
  5. customThe resulting precipitate is removed by filtration
  6. washwashed with absolute ethanol
  7. customThe filtrate is evaporated in vacuo
  8. customthe residue triturated with 5% aqueous hydrochloric acid
  9. filtrationThe aqueous suspension is filtered
  10. washthe solid washed with 5% hydrochloric acid
  11. customresulting in an oily precipitate which
  12. extractionis extracted into diethyl ether
  13. extractionThe ether extract
  14. washis washed with saturated sodium chloride solution
  15. customdried
  16. filtrationfiltered
  17. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-aa6775f96bbf48cca74b2bd5fc5ee92e
Source dataset
uspto-grants-1985_09
Patent number
US04543352

Reaction notes

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