Ammonia → Naphthalimide

HRID 842306Notes

Reaction equation

HRID 842306 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11](O[C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.[NH3:16]>O>[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([NH:16][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 6693Naphthalic anhydride

Product 1

HCID 66491NaphthalimideYield 98.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

1,8-naphthalic anhydride (50.00 g, 0.252 mol, 1.0 eq), 32.8 ml of 29% aqueous ammonia (29.52% g, or 8.56 g dry, 0.504 mol, 2.0 eq) and water (115 g) were mixed to form a yellow slurry. The yellow slurry was heated with stirring to 70° C. then held at that temperature for 90 minutes for a total heating time of about 2 hours. After the heating period, the mixture was cooled to room temperature and filtered. The product was then washed with 500 to 600 ml of water until the pH of the wash water was neutral (pH 7). The product (i.e. 1,8-naphthalimide) was isolated as a wet filtercake (59.67 g, dry content=82.28%, representing 49.10 g of dry 1,8-naphthalimide, 99% yield), which was suitable for converting to 3, 4, 9, 10-perylenetetracarboxylic diimide. The purity of 1,8-naphthalimide was above 99% as determined by Gas Chromatography with a melting point of about 301-303° C.

Workup

  1. customto form a yellow slurry
  2. temperatureThe yellow slurry was heated
  3. temperatureAfter the heating period, the mixture was cooled to room temperature
  4. filtrationfiltered
  5. washThe product was then washed with 500 to 600 ml of water until the pH of the wash water

Sources & evidence

ORD record
ord-0cde51ab81d443b2bbea9e89e9360f9f
Source dataset
uspto-grants-2002_04
Patent number
US06372910B1

Reaction notes

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