Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene | HCID 12937254 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 58980862 | HCID 58980862 | 51% |
Reaction Steps
1-(2-Bromoethoxy)2-methoxy-4-nitrobenzene (0.756 g, 2.7395 mmol) 3-pyrrolidinol (0.477 g, 5.479 mmol) and triethylamine (0.554 g, 5.479 mmol) were combined in DMF (10 mL) and heated to 80° C. The reaction was stirred for 2 h. Cooled to RT and diluted with EtOAc (100 mL) and washed with water (2×100 mL). The organics were dried over MgSO4, filtered and concentrated to afford 0.3967 g (1.407 mmol, 51%) of the desired product as a dark brown oil. 1H NMR (CDCl3) δ 7.90 (d, 1H, J=9.0 Hz), 7.75 (s, 1H), 6.93 (d, 1H, J=9.0 Hz), 4.38 (m, 1H), 4.24 (t, 2H, J=6.2 Hz), 3.95 (s, 3H), 3.2-3.0 (m, 4H), 3.0-2.90 (m, 1H), 2.8-2.70 (m, 1H), 2.60-2.50 (m, 1H), 2.30-2.20 (m, 1H), 1.85-1.75 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07285557B2 |
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| Source dataset | uspto-grants-2007_10 |
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| ORD ID | ord-ceeaa63b14c04b1d8cef824d4d87ecb2 |
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| Source note | uspto-grants-2007_10 |
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