Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | HCID 86606907 | HCID 86606907 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Product | HCID 86606906 | HCID 86606906 | 87.4% |
Reaction Steps
3-Bromo-4-hydroxybenzoic acid (4-morpholinyl)amide (286 mg, 1 mmol) is suspended in dimethylacetamide (2.9 mL), and thereto are added zinc cyanide (70 mg, 0.6 mmol), 10% Pd/C (53 mg, 0.05 mmol), zinc (36 mg, 0.56 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (28 mg, 0.05 mmol), followed by deaeration under reduced pressure for nitrogen-displacement (×3). The reaction mixture is heated at 150-155° C. and stirred for 1 hour. After cooling, the insoluble materials are removed by filtration and the reaction solution is subjected to HPLC for quantitative analysis. As a result, it is obtained 3-cyano-4-hydroxybenzoic acid (4-morpholinyl)amide (203 mg, 87.4%). Mp: 238-240° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07439368B2 |
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| Source dataset | uspto-grants-2008_10 |
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| ORD ID | ord-256673187ec7484c8befeeef4eccd7ae |
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| Source note | uspto-grants-2008_10 |
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