Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]-2-nitrobenzamide | HCID 66918925 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 66918937 | HCID 66918937 | 44.5% |
Reaction Steps
To a solution of N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]-2-nitrobenzamide (8.73 g) in methanol (250 ml) was added a saturated solution of copper acetate in water (80 ml). Sodium borohydride (4.3 g) was added portionwise and the mixture stirred for a further 1 hour at room temperature. Ethyl acetate (300 ml) was added and the mixture washed with aqueous sodium hydrogen carbonate (200 ml). The combined aqueous extracts were extracted with ethyl acetate (2×200 ml), the resulting organics washed with brine (100 ml) and dried (magnesium sulfate) and Concentrated to give the crude 2-amino-N-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-5-[(2-methylprop-2-en-1-yl)oxy]benzamide (3.6 g) as an oil which was used directly in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07750154B2 |
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| Source dataset | uspto-grants-2010_07 |
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| ORD ID | ord-0197ef1af02647dcb69dfd3b1a8128c5 |
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| Source note | uspto-grants-2010_07 |
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