2-Aminofluorene → HCID 66626347, compound

HRID 1663280Notes

Reaction equation

HRID 1663280 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[NH2:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:11]=2[CH:10]=1.C(O)(C(F)(F)F)=O>C(O)(C)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[C:12]1[C:11]2[CH:10]=[C:9]([NH2:8])[CH:21]=[CH:20][C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

5

Reactant 3

HCID 15392-AminofluoreneHCID 6422Trifluoroacetic acidHCID 73642-Thiophenecarboxaldehyde

Product 1

HCID 66626347HCID 66626347, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-Thiophenecarboxaldehyde (80.4 mg, 0.72 mmol) was added to 2-aminofluorene (100 mg, 0.55 mmol) and refluxed in isopropanol for 12 hours with a catalytic amount of TFA. The solvent was evaporated and the product was purified by flash chromatography using anhydrous basic activated alumina gel (AlO2) and 40% ethyl acetate and 60% hexanes. The title compound was obtained as a yellow product. (45.4 mg, 0.165 mmol, 30%). M.p.: 143° C. 1H-NMR (300 MHz, [D] DMSO): δ=8.65 (s, 1H), 7.89 (t, 2H, 3J=10.9 Hz), 7.81 (d, 1H, 3J=6.7 Hz), 7.69 (dd, 1H, 3J=4.8 Hz, 4J=1.4 Hz), 7.57 (d, 1H, 3J=9.76 Hz), 7.50 (s, 1H), 7.37 (t, 1H, 3J=9.88 Hz), 7.32 (t, 2H, 3J=11 Hz), 7.22 (dd, 1H, 3J=4.84 Hz, 4J=1.8 Hz), 3.94 (s, 2H). 13C-NMR (300 MHz, [D] DMSO): δ=152.9, 148.4, 144.2, 143.1, 144.4, 141.0, 129.7, 128.8, 128.2, 128.4, 127.4, 127.1, 126.8, 125.8, 123.6, 120.3, 36.5. C.V. −1.36, −0.96, −0.56, −0.02, 0.62, 1.39 V. In 0.1 M TBAPF6 as supporting electrolyte in degassed anhydrous acetonitrile λmax=352 nm. λem=302 nm. Eg=454 nm, 62.95 Kcal/mol. ΔE=300 nm, 95.26 Kcal/mol.

Workup

  1. customThe solvent was evaporated
  2. customthe product was purified by flash chromatography

Sources & evidence

ORD record
ord-67127ac76e9b4aaa93eca605b0b96ce1
Source dataset
uspto-grants-2011_10
Patent number
US08034895B2

Reaction notes

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