Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Tetramethyl orthocarbonate | HCID 74613 | — |
| Reactant | Benzoic acid, 2,3-diamino-4-methoxy-, methyl ester (9CI) | HCID 22663264 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Sodium Hydroxide | HCID 14798 | — |
| Product | HCID 178498263 | HCID 178498263 | — |
Reaction Steps
A mixture of methyl 2,3-diamino-4-methoxybenzoate [0.5 g, Reference Example 8(a)] acetic acid (0.15 ml) and tetramethoxymethane (0.53 ml) was stirred at 80° C. for 40 minutes. After cooling to room temperature the reaction mixture was diluted with a mixture of methanol (3.6 ml), 1N sodium hydroxide (2.55 ml) and water (8 ml). The resulting precipitate was filtered and then passed through a short filtration silica gel column to give the title compound (0.49 g) as a tan coloured solid. M+236. NMR (CDCl3): δ 3.93(s, 3H), 4.05(s, 3H), 4.23(s, 3H), 6.69(d, J=8 Hz, 1H), 7.74(d, J=8 Hz, 1H), 9.48(bs, 1H)].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06800645B1 |
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| Source dataset | uspto-grants-2004_10 |
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| ORD ID | ord-2fd0019fa1da49f6a7300a6d5913ae30 |
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| Source note | uspto-grants-2004_10 |
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