Hydrazine hydrate (1:1) → HCID 20138895, compound

HRID 280147Notes

Reaction equation

HRID 280147 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>[CH3:4][N:8]([CH3:7])[C:9]1([O:1][CH2:11][CH2:10][CH2:9][NH2:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

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

Product 1

HCID 20138895HCID 20138895, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

80% hydrazine hydrate (10.0 ml) is added to a stirred solution of the phthalimido tetrahydronaphthalene obtained in the previous step (52 g) dissolved in absolute ethanol (500 ml). The reaction mixture is refluxed for 3 hours, allowed to cool, and the resultant solid filtered and the filtrate evaporated in vacuo. The yellow solid residue is triturated with aqueous 5% HCl, filtered, washed with aqueous HCl, and the filtrate extracted with ether. The acidic aqueous portion is made basic with 50% sodium hydroxide. The resultant diphasic mixture is extracted with ether, the ether extracts dried, filtered, and evaporated, yielding a yellow viscous liquid (30.1 g). The liquid is dried under high vacuum, yielding 27.7 g of the crude product, which is used as is in the next step.

Workup

  1. customobtained in the previous step (52 g)
  2. temperatureThe reaction mixture is refluxed for 3 hours
  3. temperatureto cool
  4. filtrationthe resultant solid filtered
  5. customthe filtrate evaporated in vacuo
  6. customThe yellow solid residue is triturated with aqueous 5% HCl
  7. filtrationfiltered
  8. washwashed with aqueous HCl
  9. extractionthe filtrate extracted with ether
  10. extractionThe resultant diphasic mixture is extracted with ether
  11. dry with materialthe ether extracts dried
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-e7c29b2aa1b742b9913188199f036cca
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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