Hydrazine hydrate (1:1) → 1-Amino-8-(1-naphthyloxy)octane

HRID 2118659Notes

Reaction equation

HRID 2118659 reaction equation
[C:1]1([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2C(=O)C3=CC=CC=C3C2=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[NH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13520543N-8-(1-naphthyloxy)octylphthalimide

Product 1

HCID 135205411-Amino-8-(1-naphthyloxy)octane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 10.0 g N-[8-(1-naphthyloxy)octyl]phthalimide, prepared as above, and 200 ml of ethanol and 3.2 ml of hydrazine hydrate was refluxed for 18 hours. The solution was evaporated to about 100 ml, and diluted with 200 ml of water, then basified with aqueous potassium hydroxide and extracted with hexane. The extract was washed, dried and evaporated to give the title compound as an oil which was converted to the hydrochloride, mp 90.5°-92°.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe solution was evaporated to about 100 ml
  3. additiondiluted with 200 ml of water
  4. extractionextracted with hexane
  5. washThe extract was washed
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-8730f934c84d41ea84f6537e8950a6b8
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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