HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Chloride → 2-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)aniline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 4,4-Dimethyl-1-(2-nitrophenyl)-1,2,3,4-tetrahydroquinoline | HCID 57423310 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 2-(4,4-Dimethyl-3,4-dihydroquinolin-1(2H)-yl)aniline | HCID 59337707 | 73% |
Reaction Steps
The crude 1c (0.66 g) was stirred in MeOH (20 mL) at rt. Solid NH4Cl (0.62 g) was added, followed by addition of Zn dust (3.0 g) portionwise. The resulting mixture was stirred at rt for 2 h. It was filtered through Celite®, rinsed with CH2Cl2, and concentrated to dryness. The residue was purified by flash chromatography (hexanes/EtOAc) to give pure amine 1d (0.43 g, 73% for two steps). LC-MS ESI 253 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08329718B2 |
| Source dataset | uspto-grants-2012_12 |
| ORD ID | ord-766cb1a34b974b689e5e6e5f8a63d2f9 |
| Source note | uspto-grants-2012_12 |