Water → 5-Hydroxy-8H-9,11-dioxa-5-aza-benzo[de]anthracene4,6-dione

HRID 567043Notes

Reaction equation

HRID 567043 reaction equation
[CH:1]1[C:16]2[C:17]3[C:4]([C:5](=O)[O:6][C:7](=[O:18])[C:8]=3[CH:9]=[C:10]3[C:15]=2[O:14][CH2:13][O:12][CH2:11]3)=[CH:3][CH:2]=1.Cl.[NH2:21][OH:22].O>N1C=CC=CC=1>[OH:22][N:21]1[C:5](=[O:6])[C:4]2=[CH:3][CH:2]=[CH:1][C:16]3[C:17]2=[C:8]([CH:9]=[C:10]2[C:15]=3[O:14][CH2:13][O:12][CH2:11]2)[C:7]1=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 226239078H-5,9,11-trioxabenzo[de]anthracene-4,6-dione

Product 1

HCID 226239495-Hydroxy-8H-9,11-dioxa-5-aza-benzo[de]anthracene4,6-dioneYield 57.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 310 mg (1.21 mmol) of 8H-5,9,11-trioxabenzo[de]anthracene-4,6-dione (from Example T3) in 4 mL pyridine was added 260 mg (3.74 mmol) of hydroxylamine hydrochloride and the reaction mixture refluxed for 2 hours and poured into 50 mL water while hot. The precipitate was isolated, washed with water, and dried to yield 190 mg of the title compound, mp 314-315° C.

Workup

  1. temperaturethe reaction mixture refluxed for 2 hours
  2. customThe precipitate was isolated
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-e1e2c1165037471585205e8ebb6f0f33
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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