Hydroxyamine hydrochloride → HCID 178516735, compound

HRID 129443Notes

Reaction equation

HRID 129443 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-b2ba53c1c31a49e8888e0bd501cee82c
Source dataset
uspto-grants-1995_11
Patent number
US05468748

Reaction notes

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