Hexane → 4-(2-Thienyl)aniline

HRID 366861Notes

Reaction equation

HRID 366861 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.O.NN.CCCCCC>C(O)C.[Pt]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 24654Hydrazine hydrate (1:1)HCID 6095122-(4-Nitrophenyl)thiophene

Product 1

HCID 10724744-(2-Thienyl)anilineYield 98%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(2-thienyl)-4-nitrobenzene (1.65 g, 8.05 mmol) in 95% ethanol (210 mL) containing platinum on sulfide carbon (50 mg) was added hydrazine hydrate (0.5 mL). The mixture was refluxed for 2 hours. After cooling, the mixture was filtered and the solvent was evaporated to give a solid. Addition of hexane followed by filtration gave pure 1-(2-thienyl)-4-aminobenzene, yield=98%, 70-72° C. IR (KBr, in cm-1) 3440, 3344, 3098, 1620, 1500, 1281, 1183 and 813. 1H NMR (CDCl3 ; δ in ppm): 3.978 (brs, 2H), 6.670 (d, J=9.6 Hz, 2H), 7.011 (dd, J=5.6 and 4.4 Hz, 1H), 7.139 (m, 2H) and 7.382 (d, J=9.6 Hz, 2H). 13C NMR (CDCl3 ; δ in ppm): 115.07, 120.95, 122.82, 124.40, 126.91, 127.77, 144.77 and 146.46. MS(EI) m/z (rel int): 175 [(M)+, 100%], 143 [(M+ --S), 10%] and 130 [(M+ --HCS), 57%]. Anal. Calcd for C10H9NS: C, 68.53%; H 5.18; N 7.99. Found: C, 68.50; H, 5.21; N, 7.74.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customthe solvent was evaporated
  5. customto give a solid
  6. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-8fafb61e15a8414da5414a235cf864c6
Source dataset
uspto-grants-2000_10
Patent number
US06130339

Reaction notes

Loading…