Ethyl 8-(2,4-dioxo-2H-1,3-benzoxazin-3(4H)-yl)octanoate
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Chemical Product Description & Applications
Ethyl 8-(2,4-dioxo-1,3-benzoxazin-3-yl)octanoate is the N-alkylated Carsalam intermediate formed after attachment of the octanoate side chain. The benzoxazinedione ring carries the protected salicylamide unit, while the terminal ethyl ester masks the carboxylic acid. The aromatic and eight-carbon fragments are already connected through nitrogen.
This intermediate is positioned between haloester alkylation and hydrolytic conversion to the salicylamidoacid product. Opening the cyclic group restores the phenolic hydroxybenzamide functionality; hydrolysis of the ethyl ester exposes the terminal carboxyl group. These transformations provide the free acid or its sodium carboxylate, depending on work-up and salt-forming conditions. Its value lies in completing fragment assembly before those protective functions are removed.
Typical Applications
- Salcaprozic-acid preparation: Used in hydrolysis and acidification sequences that open the Carsalam-derived ring and convert the ester into 8-(2-hydroxybenzamido)octanoic acid.
- Salcaprozate-sodium process intermediates: Used upstream of alkaline conversion and sodium-salt isolation in manufacturing routes to SNAC, with the nitrogen-linked octanoate chain already installed.
Specifications
| Parameter | Specification | Test Method |
|---|---|---|
| Appearance | Solid; color consistent with the reference sample | Visual inspection |
| Identification | Consistent with authenticated reference | FTIR fingerprint comparison |
| Chromatographic purity | ≥98.0 area% | HPLC with suitable UV or CAD detection |
| Total organic impurities | ≤2.0 area% | HPLC, area normalization |
| Largest individual impurity | ≤1.0 area% | HPLC, area normalization |
| Water | ≤1.0% w/w | Karl Fischer titration |
Specifications describe the standard grade. Tolerance, test method and documentation package are confirmed per order.
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