Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 86691919 | HCID 86691919 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Product | HCID 86691918 | HCID 86691918 | 91% |
Reaction Steps
To a stirred solution of 6-methyl-3-(6-methylpyridin-3-yl)-1-nitroso-1,2,3,4-tetrahydroquinoline (0.28 g, 0.00104 mol) in acetone (15 mL) was added saturated ammonium chloride solution (0.8 mL) and water (0.8 mL) at RT. The resulting brown colored reaction mixture was cooled to 15° C. Zinc dust (0.954 g, 0.0146 mol) was added portionwise at the same temperature. After the addition, the reaction mixture was stirred for 1 h at RT. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure and the residue extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and the solvent removed under reduced pressure to obtain product as a brown colored oil (0.28 g, 91% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09193728B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-1514af0d81084e82bf04a4585ab96f95 |
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| Source note | uspto-grants-2015_11 |
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