Hydroxyamine hydrochloride → HCID 178516735, compound

HRID 263898Notes

Reaction equation

HRID 263898 reaction equation
[N:1]1[C:2]2[C:14](=O)[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:3]=2[NH:4][C:5](=[O:7])[CH:6]=1.Cl.[NH2:17][OH:18]>N1C=CC=CC=1>[OH:18][N:17]=[C:14]1[C:2]2[N:1]=[CH:6][C:5](=[O:7])[NH:4][C:3]=2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]1=2

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 190359769H-Indeno[1,2-b]pyrazine-3,9(4H)-dione

Product 1

HCID 178516735HCID 178516735, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9H-indeno[1,2-b]pyrazine-3,9(4H)-dione (1.0 g, 5.0 mmol), pyridine (40 ml) and hydroxylamine hydrochloride (0.42 g, 6.0 mmol) was stirred at 80° C. for 18 hours. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with water, acetic acid and water and dried. The crude material (0.81 g) was recrystallized from DMF to afford 0.52 g (49%) of the title compound. M.p.>300° C. 1H-NMR (DMSO-d6, δ): 7.49-7.62 (m, 2H), 7.88 (d, 1H), 7.95 (s, 1H), 8.36 (d, 1H), 12.5-13.2 (broad, 1H), 12.83 (s, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe precipitate was filtered off
  3. washwashed with water, acetic acid and water
  4. customdried
  5. customThe crude material (0.81 g) was recrystallized from DMF

Sources & evidence

ORD record
ord-1680428697604373979d32093e3e8ad5
Source dataset
uspto-grants-1997_07
Patent number
US05646146

Reaction notes

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