HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hexane → HCID 68815664, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Methyl Anthranilate | HCID 8635 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | 4-Hydroxy-3-methoxy-α-methylbenzeneacetic acid | HCID 18987074 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68815664 | HCID 68815664 | 83.7% |
Reaction Steps
The objective compound was prepared by the same procedure for the intermediate 1, using a 2-(4-hydroxy-3-methoxy-phenyl)-propionic acid (1.08 g, 5.50 mmol), SOCl2 (1.20 mL, 16.6 mmol), and 2-amino-benzoic acid methyl ester (0.56 g, 3.7 mmol). After normal workup, the pure objective compound (1.02 g, 56%) was obtained as pale yellow syrup by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.57 (d, J=7.32 Hz, 3H, CH3), 3.72 (q, J=7.32 Hz, 1H, CH), 3.85 (s, 3H, OCH3), 3.88 (s, 3H, COOCH3), 5.73 (br s, 1H, ArOH), 6.89-7.05 (m, 4H, ArH), 7.45 (t, J=8.55 Hz, 1H, ArH), 7.94 (d, J=7.73 Hz, 1H, ArH), 8.67 (d, J=8.55 Hz, 1H, ArH), 11.07 (br s, 1H, NH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07592457B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-de1be6373dba4aa88084287ff3fdc4e1 |
| Source note | uspto-grants-2009_09 |