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 extacts 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 | US07169791B2 |
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| Source dataset | uspto-grants-2007_01 |
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| ORD ID | ord-07fe145a9de54f0ab92a4dd5589afb4f |
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| Source note | uspto-grants-2007_01 |
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