Reaction #809151

Reaction equation

2,7-dinitrothianthrene

hydrazine

→

2,7-diaminothianthrene

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturethe mixture was refluxed for over night
2. 2
   Filtrationfilter through a short column of celite 545
3. 3
   OtherThe solvent was then removed
4. 4
   Otherthe resulting white solid was dried in vacuo
5. 5
   OtherIt was then recrystallized from CHCl3
6. 6
   Otherused without further purification

Procedure

To a solution of 2,7-dinitrothianthrene (550 mg, 1.8 mmole) in 100 mL of ethanol was added graphite (1.72 g, 144 mmole) and hydrazine (0.56 mL, 18 mmole) with continued stirring and the mixture was refluxed for over night. The reaction mixture was cooled to room temperature and filter through a short column of celite 545. The solvent was then removed and the resulting white solid was dried in vacuo. It was then recrystallized from CHCl3 or used without further purification. mp 185˜186° C. 1H NMR (300 MHz, CDCl3) δ: 7.15 (d, 2H, J=8.1 Hz), 6.81 (d, 2H, J=2.7 Hz), 6.52 (dd, 2H, J=8.1, 2.7 Hz), 3.68 (bs, 4H). 13C NMR (75 MHz, d6-acetone) δ: 149.5, 139.1, 130.0, 121.9, 114.8, 114.6. HR-MS (ESI): calcd. for C12H10N2S2+Na 269.0178 [(M+Na)+]. found 269.0176.

Source