HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonium Hydroxide → (+/-)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonium Hydroxide | HCID 14923 | — |
| Reactant | (+/-)-N-[(4-chlorophenyl)-(1,2-dihydro-1-methyl-2-oxo-4-phenyl-6-quinolinyl)methyl]formamide | HCID 21837469 | — |
| Solvent | Hydrochloric Acid | HCID 313 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Product | (+/-)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone | HCID 21837488 | 59% |
Reaction Steps
A mixture of intermediate (5-a) (21.2 g) in hydrochloric acid (3 N) (150 ml) and 2-propanol (150 ml) was stirred and refluxed overnight. The mixture was poured into ice, basified with NH4OH and extracted with DCM. The organic layer was dried (MgSO4), filtered off and evaporated till dryness. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98/2/0.1). The pure fractions were collected and evaporated, yielding 11.6 g (59%) of (±)-6-[amino-(4-chlorophenyl)methyl]-1-methyl-4-phenyl-2(1H)-quinolinone (interm. 5-b).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05968952 |
| Source dataset | uspto-grants-1999_10 |
| ORD ID | ord-a674ccb48a5d4b42b4843a2f5f4e2b6d |
| Source note | uspto-grants-1999_10 |