Naphthalic anhydride → N-Hydroxynaphthalimide

HRID 127984

Reaction equation

HRID 127984 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[CH:7]1[CH:12]=[C:11]2[C:13]([O:15][C:16]([C:18]3=[CH:19][CH:20]=[CH:21][C:9](=[C:10]23)[CH:8]=1)=O)=[O:14].Cl.[NH2:23][OH:24]>>[CH:7]1[CH:12]=[C:11]2[C:13]([N:23]([OH:24])[C:16]([C:18]3=[CH:19][CH:20]=[CH:21][C:9](=[C:10]23)[CH:8]=1)=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 6693Naphthalic anhydrideHCID 10340Sodium Carbonate2×HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 82263N-Hydroxynaphthalimide

Procedure

To 400 g of an aqueous solution of 3% by weight sodium carbonate were added 24.0 g of 1,8-naphthalic acid anhydride and 10.0 g of hydroxylamine hydrochloride and they were reacted for 2 hours at 90° C. Then, 200 g of an aqueous solution of 10% by weight sodium carbonate was added to the mixture, after filtering away insoluble materials, 100 ml of concentrated hydrochloric acid was added to the mixture, and precipitates formed were collected and recrystallized from ethanol to provide N-hydroxy-1,8-naphthalimide.

Workup

  1. customwere reacted for 2 hours at 90° C
  2. filtrationafter filtering away insoluble materials, 100 ml of concentrated hydrochloric acid
  3. additionwas added to the mixture
  4. customprecipitates
  5. customformed
  6. customwere collected
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-855ec7073a8a4488a053b4ad8e662956
Source dataset
uspto-grants-1981_03
Patent number
US04258121

Linked notes

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