Water → HCID 22623957, compound

HRID 567042Notes

Reaction equation

HRID 567042 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][CH2:12][O: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][CH2:12][O:11]2)[C:7]1=[O:18]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 22623975HCID 22623975, compound

Product 1

HCID 22623957HCID 22623957, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 70 mg (0.27 mmol) of 9H,10H-5,8,11-trioxabenzo[de]anthracene-4,6-dione (from Example R3) in 4 mL pyridine was added 80 mg (1.16 mmol) of hydroxylamine hydrochloride and the reaction mixture refluxed for 1.5 hours and poured into 20 mL water while hot. The precipitate was isolated after 24 hours, washed with water, 1% HCl, water, and dried to yield 71 mg of the title compound, mp 344-347° C.

Workup

  1. temperaturethe reaction mixture refluxed for 1.5 hours
  2. customThe precipitate was isolated after 24 hours
  3. washwashed with water, 1% HCl, water
  4. customdried

Sources & evidence

ORD record
ord-f07b2652c64b45ecb2c43e53ecce44b8
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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