HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Amino-2-methylphenol → 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 5-Amino-2-methylphenol | HCID 17818 | — |
| Reactant | Oxalyl chloride | HCID 65578 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 3-(1-Cyanocyclopropyl)benzoic acid | HCID 57441039 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methylphenyl)benzamide | HCID 67312557 | 87.5% |
Reaction Steps
Using 5-amino-2-methylphenol (6.00 g, 48.5 mmol), 3-(1-cyanocyclopropyl)benzoic acid (6.00 g, 48.5 mmol) produced in Example A1(iii), oxalyl chloride (6.40 mL, 73.0 mmol), N,N-dimethylformamide (40 μL), tetrahydrofuran (250 mL), sodium hydrogencarbonate (6.20 g, 73.0 mmol) and water (60 mL) as starting materials, and in the same manner as in Example A32(i), the title compound (12.4 g, 87%) was obtained as a white powder. The title compound was washed with a mixed solvent of ethyl acetate and hexane.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08324395B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-9d7c02803abc4c4691af04383fdd01f5 |
| Source note | uspto-grants-2012_12 |