Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | Potassium Bromide | HCID 253877 | — |
| Reactant | HCID 85909722 | HCID 85909722 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 59631412 | HCID 59631412 | — |
Reaction Steps
A mixture of 3-(4-morpholinyl)-5-nitro-benzoic acid, 1,1-dimethylethyl ester (Example 87b; 0.77 g, 2.5 mmol), 1,8-diazabicyclo[5,4,0]undec-7-ene (0.56 mL, 3.75 mL), and potassium bromide (1.09 g, 12.5 mmol) in methanol (25 mL) is stirred at 90° C. for 250 min. The cooled mixture is then added to hydrochloric acid (50 mL of 0.1 M) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with saturated aqueous sodium hydro-carbonate (2×25 mL), water (2×25 mL) and brine (2×50 mL), dried (MgSO4) and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ethyl acetate—hexane to afford the title compound as yellow crystalline solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07569566B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-0eb54982a69744c28ae3509a7e155d51 |
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| Source note | uspto-grants-2009_08 |
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