Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexanol | HCID 7966 | — |
| Reactant | Hydrazinecarboxaldehyde | HCID 12229 | — |
| Reactant | 6-Bromo-3,4-dihydroquinoline-2(1H)-thione | HCID 57370990 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 21543699 | HCID 21543699 | — |
Reaction Steps
A flask containing the title compound from Example 22, Step A (0.200 g, 0.826 mmol), formic hydrazide (0.099 g, 1.65 mmol) and cyclohexanol (6.00 ml, 0.826 mmol) was heated to 120° C. for 16 hours. The reaction was then cooled to room temperature, poured into water and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (0-15% methanol in ethyl acetate) provided the title compound: LCMS m/z 251.90 [M+2+H]+; 1H NMR (500 MHz, CD3OD) δ 9.12 (s, 1H), 7.63-7.54 (m, 3H), 3.19-3.16 (m, 2H), 3.11-3.08 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09073929B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-6be06c346f4441fb80c58f88157a67a7 |
|---|
| Source note | uspto-grants-2015_07 |
|---|