HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzoyl Peroxide → Glycine, N-methyl-, ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzoyl Peroxide | HCID 7187 | — |
| Reactant | Ethyl 2-methylbenzoate | HCID 66598 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 2,3,7,11b-Tetrahydro-1H-dibenzo[de,h]isoquinoline-8,9-diol | HCID 5249490 | — |
| Reactant | Dinapsoline | HCID 9816455 | — |
| Reactant | 2-Methyl-2,3-dihydroisoquinolin-4(1H)-one | HCID 10630812 | — |
| Product | Glycine, N-methyl-, ethyl ester | HCID 95849 | — |
| Product | Dinapsoline | HCID 9816455 | — |
Reaction Steps
One compound provided in accordance with the present invention is (±)-8,9-dihydroxy-2,3,7,11b-tetrahydro-1H-naphtho[1,2,3-de] isoquinoline denominated hereinafter as “dinapsoline.” Dinapsoline is synthesized from 2-methyl-2,3-dihydro-4(1H)-isoquinolone according to the procedure depicted generally in FIGS. 1 and 2. Side chain bromination of ethyl-o-toluate (5a) with NBS in the presence of benzoyl peroxide produced compound 5b. Alkylation of sarcosine ethyl ester with compound 5b afforded compound 6, which after Dieckmann condensation and subsequent decarboxylation on acidic hydrolysis yielded compound 7.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06194423B1 |
| Source dataset | uspto-grants-2001_02 |
| ORD ID | ord-20c0db3282de49a1a45ad3080f2e2a79 |
| Source note | uspto-grants-2001_02 |