HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrazine → 4-(Octyloxy)-3-(trifluoromethyl)benzohydrazide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrazine | HCID 9321 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 4-Octyloxy-3-trifluoromethylbenzoic acid | HCID 53349255 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | dichloromethane N,N-dimethylformamide | HCID 22350042 | — |
| Product | 4-(Octyloxy)-3-(trifluoromethyl)benzohydrazide | HCID 53349360 | 105.2% |
Reaction Steps
4-(Octyloxy)-3-(trifluoromethyl)benzoic acid (11a) (632 mg, crude, approximately 1.89 mmol) was stirred with HATU (905 mg) and DIEA (1.7 mL) in CH2Cl2-DMF (10 mL, 4:1) for 10 min followed by addition of hydrazine (297 μL) dropwise. The reaction mixture was continuously stirred for another hour, then was diluted with ethyl acetate (30 mL) and washed with water (10 mL) and brine (3×15 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo to afford the title compound (661 mg, HPLC purity >90%), which was used for next reaction without further purification. MS (ESI): 333.08 (MH+); HPLC retention time on a C8(2) column (30×3.00 mm, 3μ) is 1.61 min with gradient 50-98% acetonitrile-H2O (0.1% TFA) in 3.5 min as mobile phase.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07759370B2 |
| Source dataset | uspto-grants-2010_07 |
| ORD ID | ord-56b50cc8ab754905b829b59d7c0d9932 |
| Source note | uspto-grants-2010_07 |