N-[2-(9-anthryloxy)ethyl]phthalimide → Ammonium Hydroxide

HRID 414477Notes

Reaction equation

HRID 414477 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[O:15][CH2:16][CH2:17][N:18]2C(=O)C4=CC=CC=C4C2=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1>C(O)C.C(OCC)(=O)C>[OH-:15].[NH4+:18].[CH:11]1[C:12]2[C:7](=[CH:6][C:5]3[C:14]([C:13]=2[O:15][CH2:16][CH2:17][NH2:18])=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 1

HCID 14373233N-[2-(9-anthryloxy)ethyl]phthalimide

Product 2

HCID 14923Ammonium HydroxideHCID 143732341-(9-Anthryloxy)-2-aminoethane

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[2-(9-anthryloxy)ethyl]phthalimide (6.5 g) was refluxed for 3 hours in ethanol containing 85% hydrazine hydrate (3.0 ml). The solution was cooled and diluted with ethyl acetate. The resultant solution was washed with dilute aqueous potassium hydroxide, dried and evaporated. The crude product was chromatographed on 300 g silica gel, eluting with a solution of methylene chloride:methanol:ammonium hydroxide, 95:4:1, yielding 1-(9-anthryloxy)-2-aminoethane, which was converted to the maleate, mp 190°-195° C., according to the method of Example 3.

Workup

  1. temperatureThe solution was cooled
  2. washThe resultant solution was washed with dilute aqueous potassium hydroxide
  3. customdried
  4. customevaporated
  5. customThe crude product was chromatographed on 300 g silica gel
  6. washeluting with a solution of methylene chloride

Sources & evidence

ORD record
ord-e0ad50f2f3474ce98cbd9698019241a7
Source dataset
uspto-grants-1988_12
Patent number
US04792551

Reaction notes

Loading…