2(1H)-Quinoxalinone, 3,4-dihydro- → 4-Nitroso-3,4-dihydroquinoxalin-2(1H)-one

HRID 717765

Reaction equation

HRID 717765 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][C:2]1=[O:11].[N:12]([O-])=[O:13].[Na+]>Cl.O>[N:12]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:1][C:2](=[O:11])[CH2:3]1)=[O:13]

Participants

5

Reactant 2

HCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-HCID 23668193Sodium Nitrite

Product 1

HCID 131503004-Nitroso-3,4-dihydroquinoxalin-2(1H)-oneYield 66.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

3,4-Dihydro-1H-quinoxalin-2-one (500 mg, 3.378 mmol) was dissolved in 3N HCl (10 mL) and stirred for 5 min. at 0° C. A solution of sodium nitrite (256 mg, 3.716 mmol) in water (2 mL) was added at 0° C., and the reaction mixture was stirred for 2 h at RT. After completion of reaction, water was added and the mixture extracted twice with DCM (100 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 400 mg of 3,4-dihydro-4-nitrosoquinoxalin-2(1H)-one.

Workup

  1. stirringthe reaction mixture was stirred for 2 h at RT
  2. additionwas added
  3. extractionthe mixture extracted twice with DCM (100 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-24f5d11fe391424b8550b68b20cabb37
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Linked notes

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