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Water → 3-(4-chlorophenyl)-1-ethyl-quinoxalin-2(1H)-one

HRID 1961563
Notes
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Reaction equation

HRID 1961563 reaction equation
Br[C:2]1[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:18][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 581109523-bromo-1-ethyl-quinoxalin-2(1H)-one

Product 1

HCID 442253923-(4-chlorophenyl)-1-ethyl-quinoxalin-2(1H)-oneYield 59%

Reagents, catalysts & solvents 2

HCID 6102075
Dichlorobis(triphenylphosphine)palladium
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 200 mg (0.79 mM) of 3-bromo-1-ethyl-quinoxalin-2(1H)-one and 27.7 mg (0.04 mM) of bis(triphenylphosphine)palladium (II) chloride in 1 ml of dimethylformamide were added under nitrogen 185,3 mg (1,185 mM) of 4-chlorophenylboronic acid and 0,8 ml (1,6 mM) of a 2M sodium carbonate aqueous solution. The reaction mixture was heated to 90° C. and stirred for 30 min under nitrogen atmosphere. Water was added and the mixture was extracted with ethyl acetate. The organic phase was separated, dried over anhydrous sodium sulfate, and concentrated. The compound was purified through a silica plug eluting with dichloromethane, which afforded after evaporation 132 mg of 3-(4-chlorophenyl)-1-ethyl-quinoxaline-2(1H)-one as a solid. Yield: 59%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic phase was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe compound was purified through a silica plug
  6. washeluting with dichloromethane, which
  7. customafforded
  8. customafter evaporation 132 mg of 3-(4-chlorophenyl)-1-ethyl-quinoxaline-2(1H)-one as a solid

Sources & evidence

ORD record
ord-56fdbb8c65a14c5a9dcf4debdecd1761
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08415352B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes