Sodium Hydroxide → 3-(2-quinoxalinyl)aniline

HRID 2045910Notes

Reaction equation

HRID 2045910 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:19]=[N:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl[Sn]Cl.O.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:18]=[CH:19][C:10]=1[C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 7377362-(3-nitrophenyl)quinoxalineHCID 43835034Tin dichloride dihydrate

Product 1

HCID 8072643-(2-quinoxalinyl)anilineYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(3-nitrophenyl)quinoxaline (9.4 g, 37.4 mmol), SnCl2.H2O (28 g, 13.48 mmol) in CHCl3 (95 mL) was heated to 90° C. for 15 minutes, cooled to room temperature, added to ice water (190 mL), and basified to pH 10 with 50% aqueous NaOH, adding ice as necessary to maintain the temperature below 10° C. The mixture was extracted with ethyl acetate (500 mL), and the organic phase was filtered through a Celite pad, which was washed once with ethyl acetate (150 mL). The combined organics phases were washed with brine and dried, and then solvent was evaporated in vacuo. The resulting solid was recrystallized from toluene to afford (3-quinoxalin-2-ylphenyl)amine (5.6 g, 68% yield). LCMS calculated for C14H11N3 (M+H): 222.26. found 222. 1H-NMR (400 MHz, DMSO-d6) δH: 9.42 (1H, s), 8.11-8.00 (2H, m), 7.94-7.75 (2H, m), 7.55 (1H, s), 7.42 (1H, d, J=7 Hz), 7.22 (1H, m), 6.72 (1H, m), 5.42 (2H, br. s).

Workup

  1. additionadding ice as necessary
  2. temperatureto maintain the temperature below 10° C
  3. extractionThe mixture was extracted with ethyl acetate (500 mL)
  4. filtrationthe organic phase was filtered through a Celite pad, which
  5. washwas washed once with ethyl acetate (150 mL)
  6. washThe combined organics phases were washed with brine
  7. customdried
  8. customsolvent was evaporated in vacuo
  9. customThe resulting solid was recrystallized from toluene

Sources & evidence

ORD record
ord-4dfdf1bf8a7d4b5babcfc747c4e1703a
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

Loading…