Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 4,6-Dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine | HCID 14055338 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86704558 | HCID 86704558 | 93.6% |
Reaction Steps
A microwave reaction vial was charged with 4,6-dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine (60 mg, 0.29 mmol), a 2M aqueous sodium hydroxide solution (10 mL) and 1,4-dioxane (1 mL). The vial was sealed and then heated in the microwave at 160° C. for 30 min. At this time, the resulting mixture was acidified to pH 6.5 with a 4M aqueous hydrochloric acid solution and then concentrated in vacuo. The residue was diluted with ethanol. The solids were removed by filtration, and the filtrate was concentrated in vacuo. Flash chromatography (10/1 methylene chloride/methanol) afforded 6-chloro-1-methyl-1,5-dihydro-pyrrolo[3,2-c]pyridine-4-one (51 mg, 93.6%). LC-MS calcd. for C8H7ClN2O2 [(M+H)+] 183, obsd. 182.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08722661B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-6fff99f580fa41e3afd804b19a0f18c9 |
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| Source note | uspto-grants-2014_05 |
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