Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | HCID 86628684 | HCID 86628684 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 76540061 | HCID 76540061 | 69% |
Reaction Steps
Method Z-2 Place N-[3-(4-formyl-phenyl)-1-isopropyl-1H-indol-6-yl]-methanesulfonamide and hydroxylamine hydrochloride into a round bottom flask under nitrogen. Add ethanol (10 mL), tetrahydrofuran (10 mL) and pyridine. Warm to 60° C., and stir for 2 hours. Dilute with ethyl acetate (20 mL), and wash with 1N hydrochloric acid. Dry the organic layer over sodium sulfate, and concentrate in vacuo. Purify the residue by flash chromatography on silica (5-40% ethyl acetate in dichloromethane) to give N-{3-[4-(Hydroxyimino-methyl)-phenyl]-1-isopropyl-1H-indol-6-yl}-methanesulfonamide (241.1 mg, 69%). LRMS (API ES+)=372.0 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07932284B2 |
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| Source dataset | uspto-grants-2011_04 |
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| ORD ID | ord-05a13021ecc040ef80959690b904df72 |
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| Source note | uspto-grants-2011_04 |
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