Hexane → 4-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)aniline

HRID 366863Notes

Reaction equation

HRID 366863 reaction equation
[CH2:1]1[CH2:9][O:8][C:7]2[C:3](=[C:4]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=3)[S:5][CH:6]=2)[O:2]1.O.NN.CCCCCC>C(O)C.[Pt]>[CH2:1]1[CH2:9][O:8][C:7]2[C:3](=[C:4]([C:10]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=3)[S:5][CH:6]=2)[O:2]1

Participants

6

Reactant 3

HCID 8058HexaneHCID 24654Hydrazine hydrate (1:1)HCID 154774201-(3,4-Ethylenedioxythien-2-yl)-4-nitrobenzene

Product 1

HCID 154774214-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)anilineYield 66%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(3,4-ethylenedioxythien-2-yl)-4-nitrobenzene (0.663 g, 2.52 mmol) in 95% ethanol (60 mL) containing platinum on sulfide carbon (50 mg) was added hydrazine hydrate (1.0 mL). The mixture was refluxed for 10 hours. After cooling, the mixture was filtered and the solvent was evaporated to give a solid. Addition of hexane followed by filtration gave 1-(3,4-ethylenedioxythien-2-yl)-4-aminobenzene. It was recrystallized from ethanol, 0.39 g, yield=66%, mp=98.5-99° C. IR (KBr; cm-1) 3433, 3352, 3032, 2924, 1624, 1520, 1428, 1365, 1288, 1170, 1071, 920 and 833. 1H NMR(CDCl3 ; δ in ppm): 3.604 (br, s, 2H), 4.208 (m, 4H), 6.176 (s, 1H), 6.651 (d, J=9.6 Hz, 2H) and 7.492 (d, J=9.6 Hz, 2H). 13C NMR(CDCl3 ; δ in ppm): 64.45, 64.59, 95.61, 115.10, 117.98, 123.60, 127.25, 136.61, 142.09 and 145.20. MS(EI) m/z (rel int): 233 [(M)+, 55%], 177 [(M+ --C3H4O), 6.6%], 149 [(M+ --C4H4O2, 11%] and 136 [(M+ --C5H5O2) 100%]. Anal. Calcd for C12H11NO2S: C, 61.78; H, 4.75; N, 6.00; S, 13.74. Found: C, 60.82; H. 4.87; N, 5.64; S, 12.86.

Workup

  1. temperatureThe mixture was refluxed for 10 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-d6b9c855181d4a8b8d45753d35b6852e
Source dataset
uspto-grants-2000_10
Patent number
US06130339

Reaction notes

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