HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aniline → 1H-1,2-Diazepine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aniline | HCID 6115 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Trimethyl orthoformate | HCID 9005 | — |
| Reactant | 1H-1,2-Diazepine | HCID 166734 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | Ammonium Hydroxide | HCID 14923 | — |
| Product | 1H-1,2-Diazepine | HCID 166734 | 70% |
Reaction Steps
Aldehyde 160 (1.08 g, 3.0 mmol) was converted at 25° C. by standard procedures to amine 161, using 99:1 trimethylorthoformate:acetic acid as solvent (20 mL), 1.1 equivalents of aniline (3.3 mmol), and after 1 hour adding 1.5 equivalents (8.9 mmol) of commercial 1M sodium cyanoborohydride THF solution. Aqueous workup and silica gel chromatography (eluent: 90:10:1 ethyl acetate:hexane:ammonium hydroxide) gave amine 161 as a colorless foam (0.93 g, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07129228B2 |
| Source dataset | uspto-grants-2006_10 |
| ORD ID | ord-c5508f601a8a42c980970a95f8a33705 |
| Source note | uspto-grants-2006_10 |