Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 69671083 | HCID 69671083 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Hydrogen chloride-ethyl acetate | HCID 21866389 | — |
| Product | HCID 69671353 | HCID 69671353 | 17.7% |
Reaction Steps
A mixture of 6-(4-methoxy-3-nitrophenyl)-3-(2-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine (80 mg, 0.21 mmol), iron (59 mg, 1.06 mmol) and NH4Cl (6 mg, 0.11 mmol) in ethanol (10 mL) and water (10 ml) was stirred for 3 h at 70° C. The mixture was concentrated under reduced pressure at 50° C. to remove ethanol, and was extracted with ethyl acetate (40 mL×4). The combined organic phase were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a product. The product was dissolved in HCl/ethyl acetate (2M, 20 mL), stirred at room temperature for 30 min, and concentrated to dryness to give the title compound (7.45 mg, 10.2% yield) as yellow solids. 1H NMR (DMSO-d6): 8.14 (m, 1H), 8.05 (dd, J=9.6 and 0.9 Hz, 1H), 7.88 (dd, J=9.6 and 1.5 Hz, 1H), 7.71-7.58 (m, 4H), 7.35 (d, J=8.1 Hz, 1H), 7.26-7.19 (m, 2H), 3.92 (s, 3H), 3.89 (s, 3H). MS: m/z 347.2 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09199983B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-08b0cf30219f4cce8e13ea7768e875d9 |
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| Source note | uspto-grants-2015_12 |
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