HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → 6-Methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Phosphorus oxide (P4O10) | HCID 14812 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | N-[2-(3-methyl-4-methoxyphenyl)ethyl]-3-(4-chlorophenyl)propionamide | HCID 19892235 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | O-Xylene | HCID 7237 | — |
| Product | 6-Methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinoline | HCID 19739693 | 52.3% |
Reaction Steps
Heat a mixture of the amide from step A (10.0 g), phosphorous pentoxide (25 g), phosphorous oxychloride (15 mL) and xylene (250 mL) at reflux for 2 h. Cool the reaction mixture, slowly add water (500 mL), basify using NaOH and extract with benzene. Concentrate the benzene extract to a residue and triturate with diethyl ether to give 6-methyl-7-methoxy-1-[2-(4-chlorophenyl)ethyl]-3,4-dihydroisoquinoline (4.95 g), mp=122°-124° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05124337 |
| Source dataset | uspto-grants-1992_06 |
| ORD ID | ord-33fd2248f5164c60acda88d87f0ff315 |
| Source note | uspto-grants-1992_06 |