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Tolazoline → 1,2-Dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide

HRID 2309687
Notes
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Reaction equation

HRID 2309687 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([CH2:7][C:8]2[NH:12][CH2:11][CH2:10][N:9]=2)=[CH:5][CH:6]=1.F[C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[N+:21]([O-])=[O:22].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)C>[F:20][C:18]1[CH:19]=[C:14]2[C:15]([N+:21]([O-:22])=[C:7]([C:4]3[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=3)[C:8]3[N:9]2[CH2:10][CH2:11][N:12]=3)=[CH:16][CH:17]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5504TolazolineHCID 11430Potassium CarbonateHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 139586071,2-Dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxideYield 54.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of tolazoline (40 g, 0.25 mol), 2,4-difluoronitrobenzene (39.75 g, 0.25 mol) and potassium carbonate (17.26 g, 0.125 mol) in isopropanol (500 ml) was heated to 50° C. for a period of two days. The solvent was removed in vacuo from the mixture and the residue was dissolved in dichloromethane. The resulting solution was filtered and the solvent removed in vacuo to yield a yellow solid which was chromatographed on silica gel using 2% methanol/chloroform as the eluent to yield 1,2-dihydro-8-fluoro-4-phenylimidazo[1,2-a]quinoxaline 5-oxide (38.5 g) as an orange solid, having a m.p. 188°-193° C., (Found: C, 68.07; H 4.23; N 14.82%; C16H12FN3O requires C 68.33; H 4.27; N 14.95%) and represented by the structural formula ##STR14##

Workup

  1. customThe solvent was removed in vacuo from the mixture
  2. dissolutionthe residue was dissolved in dichloromethane
  3. filtrationThe resulting solution was filtered
  4. customthe solvent removed in vacuo
  5. customto yield a yellow solid which
  6. customwas chromatographed on silica gel using 2% methanol/chloroform as the eluent

Sources & evidence

ORD record
ord-657c238ee8d54bd9a75a8cb92122b09f
Source dataset
uspto-grants-1987_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04696928

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes