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3-Phenyl-3,4-dihydroquinoxalin-2(1H)-one → 3,4-dihydro-4-nitroso-3-phenylquinoxalin-2(1H)-one

HRID 717766
Notes
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Reaction equation

HRID 717766 reaction equation
[C:1]1([CH:7]2[NH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:18]([O-])=[O:19].[Na+]>Cl.O>[N:18]([N:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8](=[O:17])[CH:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 126318403-Phenyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 23668193Sodium Nitrite

Product 1

HCID 866919253,4-dihydro-4-nitroso-3-phenylquinoxalin-2(1H)-oneYield 98.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A suspension of 3,4-dihydro-3-phenylquinoxalin-2(1H)-one (430 mg, 1.9 mmol) in 3N HCl (30 mL) was stirred at 5° C. Sodium nitrite (150 mg, 2.17 mmol) in water (1 mL) was added dropwise and stirring was continued for 1 h. The reaction mixture was extracted with DCM. The organic layer was dried over sodium sulfate and concentrated under vacuum to obtain 475 mg of 3,4-dihydro-4-nitroso-3-phenylquinoxalin-2(1H)-one.

Workup

  1. stirringstirring
  2. extractionThe reaction mixture was extracted with DCM
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4910e04cf3554487954978c388293052
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09193728B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes