HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N-[6-(azidomethyl)-1-isoquinolinyl]benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 1,8-Diazabicyclo(5.4.0)undec-7-ene | HCID 81184 | — |
| Reactant | P,P-Diphenylphosphinic azide | HCID 199401 | — |
| Reactant | N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamide | HCID 22665633 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-[6-(azidomethyl)-1-isoquinolinyl]benzamide | HCID 22665816 | — |
Reaction Steps
To 6.3 g of N-[6-(hydroxymethyl)-1-isoquinolinyl]benzamide (1 g) in 40 mL of toluene and 40 mL of dioxane at 0° C. 7.8 mL of diphenylphosphoryl azide (DDPA) and 5.4 mL of 1,8-diazabicyclo(5.4.0)undec-7ene (DBU) were added. After 24 hours the reaction mixture was poured into water (pH 7) and extracted with ethyl acetate. The organic layer was dried (sodium sulfate) and concentrated. Trituration with diethyl ether gave 6.4 g of the title compound. Mp. 125-129° C. MS (m/e)=303.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06444672B1 |
| Source dataset | uspto-grants-2002_09 |
| ORD ID | ord-0eec1549446046789ce4251ca1a3c85d |
| Source note | uspto-grants-2002_09 |