Hydroxyamine hydrochloride → HCID 178518602, compound

HRID 235300Notes

Reaction equation

HRID 235300 reaction equation
[NH2:1][C:2]1[C:3](=[O:12])[NH:4][C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.N[OH:15]>C(O)CCC>[OH:15][N:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 47380403-Aminoquinoxalin-2(1H)-one

Product 1

HCID 178518602HCID 178518602, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
25 °C

Procedure

An adaptation of the method of Harsanyi et al., Liebigs Ann. Chem. 190 (1973), was used. A mixture of 3-aminoquinoxalin-2(1H)-one (1) (100 mg, 0.620 mmol) and hydroxylamine hydrochloride (94 mg, 1.3 mmol; Aldrich Co.) in 5 mL of 1-butanol was heated to reflux. The resulting suspension was stirred under reflux for 12 h. The resulting suspension was cool to 25° C. A pale yellow precipitate appeared. The mixture was vacuum filtered and the solid was washed with EtOH (5×2 mL) and dried in vacuum at 60° C. overnight to yield 5 mg (42%) of 3-(hydroxyimino)-1,4-dihydroquinoxalin-2-one as a pale yellow solid mp dec.>330° C. 1H NMR (300 MHz, DMSO-d6) δ 11.156 (br s, 1H, NOH), 10.776 (br s, 1H, NH), 9.878 (br s, 1H, NH), 7.258-6.813 (m, H, H-5+H-6+H-7+H-8). LRMS: 177 (M+, 78%), 161 (100%).

Workup

  1. temperaturewas heated to reflux
  2. temperatureunder reflux for 12 h
  3. filtrationfiltered
  4. washthe solid was washed with EtOH (5×2 mL)
  5. customdried in vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-d28ec9cc9bce4bd5bf547108fac43dad
Source dataset
uspto-grants-1997_01
Patent number
US05597922

Reaction notes

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