HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → HCID 18435892, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Nitric Acid | HCID 944 | — |
| Reactant | Potassium Nitrate | HCID 24434 | — |
| Reactant | 8-Methylisoquinoline | HCID 3017364 | — |
| Solvent | Sulfuric Acid | HCID 1118 | — |
| Product | HCID 18435892 | HCID 18435892 | — |
Reaction Steps
In Scheme 12, the 8-methylisoquinoline (obtained as described above) is nitrated with a suitable nitrating agent such as potassium nitrate in sulfuric acid or a mixture of nitric acid, sulfuric acid and acetic acid to yield 5-nitro-8-methylsioquinoline, which is reduced and then acetylated to give the N-(8-methyl-isoquinolin-5-yl)-acetamide. This amide may be brominated by a radical brominating agent such as N-bromosuccinimide/benzoyl peroxide to give the dibromo isoquinoline acetamide. The dibromo intermediate may then be hydrolyzed in the presence of base to yield the deprotected aldehyde aminoisoquinoline, which may be further elaborated by the chemistry illustrated in Schemes 5 and 6 to the target ureas.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07183411B2 |
| Source dataset | uspto-grants-2007_02 |
| ORD ID | ord-710ce2747b6348859277892b350d92a6 |
| Source note | uspto-grants-2007_02 |