Ammonium Hydroxide → Acenaphthene-1,2-dicarboximide

HRID 1973447

Reaction equation

HRID 1973447 reaction equation
[CH:1]1([C:16]([OH:18])=O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH:2]1[C:13](O)=[O:14].[OH-].[NH4+:20]>>[CH:1]12[C:16](=[O:18])[NH:20][C:13](=[O:14])[CH:2]1[C:3]1[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]2=3)[CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 27543701,2-Acenaphthylenedicarboxylic acid, 1,2-dihydro-

Product 1

HCID 21491653Acenaphthene-1,2-dicarboximide

Conditions

Temperature
200 °C

Procedure

5.5 Parts of acenaphthene-1,2-dicarboxylic acid is heated in an oil bath with an excess of concentrated ammonium hydroxide. After most of the excess of ammonium hydroxide has distilled off, the temperature of the oil bath is raised to 200° C. and it is maintained at that temperature for 45 minutes. The residual material is sublimed under vacuum (0.05-0.1 mm.) using an oil bath at 280° C. The resultant solid is recrystallized from ethanol to give acenaphthene-1,2-dicarboximide melting at about 242°-246° C.

Workup

  1. distillationAfter most of the excess of ammonium hydroxide has distilled off
  2. temperatureit is maintained at that temperature for 45 minutes
  3. customat 280° C
  4. customThe resultant solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-1b7a22926b3049d7860d79389db5a896
Source dataset
uspto-grants-1976_12
Patent number
US03997572

Linked notes

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