Water → N-[8-(2-naphthyloxy)octyl]phthalimide

HRID 2118661Notes

Reaction equation

HRID 2118661 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1.[C:21]1(=[O:31])[NH:25][C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]12.[K].O>CN(C)C=O>[CH:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][C:11]=1[O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:25]1[C:24](=[O:26])[C:23]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:22]2[C:21]1=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 135205391-(2-Naphthyloxy)-8-chlorooctaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 20192898N-[8-(2-naphthyloxy)octyl]phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-8-(2-naphthyloxy)octane (4.75 g) and potassium phthalimide (4.2 g) were heated in dimethylformamide (25 ml) at 120° for 4 hours. The solution was then cooled, added to water, and extracted with methylene chloride. The extracts were then dried and evaporated to afford N-[8-(2-naphthyloxy)octyl]phthalimide as a gum. This material was refluxed for 16 hours in ethanol (150 ml) containing 85% aqueous hydrazine hydrate (3 ml). The solution was cooled and water (450 ml) and 10% aqueous potassium hydroxide (50 ml) were added. The resultant solution was extracted with hexane; the extract was dried and evaporated to afford the title compound as an oil (hydrochloride mp 169°-170°).

Workup

  1. temperatureThe solution was then cooled
  2. extractionextracted with methylene chloride
  3. customThe extracts were then dried
  4. customevaporated

Sources & evidence

ORD record
ord-5c4bfcafb4114c26b1d3b2c273ac3c19
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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