Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | HCID 22556762 | HCID 22556762 | — |
| Catalyst | HCID 178505374 | HCID 178505374 | — |
| Solvent | Quinoline | HCID 7047 | — |
| Product | HCID 21818461 | HCID 21818461 | 61.1% |
Reaction Steps
A mixture of 4,5-dihydro-pyrrolo[3,2,1-hi]indole-2-carboxylic acid (120 mg, 0.64 mmol) and copper chromite (50 mg) in quinoline (5 ml) in a sealed vessel was heated to 200° C. in a microwave for 20 minutes. After cooling to room temperature the mixture was poured into ethyl acetate (100 ml) and washed with 1M hydrochloric acid (3×100 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was purified by preparative thin layer chromatography (SiO2, 20% EtOAc in hexanes) to yield 1,2-dihydro-pyrrolo[3,2,1-hi]indole as a pale yellow crystalline solid (56 mg). 400 MHz 1H NMR (CDCl3) δ: 7.33 (d, J=8.0 Hz, 1H), 7.14 (d, J=2.8 Hz, 1H), 7.04-6.97 (m, 1H), 6.91 (d, J=6.8 Hz, 1H), 6.44 (d, J=2.8 Hz, 1H), 4.51 (t, J=7.2 Hz, 2H), 3.80 (t, J=7.2 Hz, 2H); LCMS: 144 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08513292B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-0a0f6547f5ab43faa2d4f6bf0660850b |
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| Source note | uspto-grants-2013_08 |
|---|