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| | 2-Amino-5-methoxybenzoic acid Basic information |
| | 2-Amino-5-methoxybenzoic acid Chemical Properties |
| Melting point | 148-152 °C | | Boiling point | 349.9±27.0 °C(Predicted) | | density | 1.303±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,Room temperature | | solubility | Methanol (Slightly) | | form | Crystalline Powder | | pka | 2.08±0.10(Predicted) | | color | White to yellow to pale orange | | BRN | 777690 | | InChI | InChI=1S/C8H9NO3/c1-12-5-2-3-7(9)6(4-5)8(10)11/h2-4H,9H2,1H3,(H,10,11) | | InChIKey | UMKSAURFQFUULT-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC(OC)=CC=C1N | | CAS DataBase Reference | 6705-03-9(CAS DataBase Reference) | | NIST Chemistry Reference | 5-Methoxyanthranilic acid(6705-03-9) |
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ALFA
| English |
| | 2-Amino-5-methoxybenzoic acid Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | 2-Amino-5-methoxybenzoic Acid is used in the synthesis of quinazolinone class of histamine H3 receptor inverse agonists. It is also used in the synthesis of Alogliptin, a selective inhibitor of the s
erine protease dipeptidyl peptidase IV. | | Uses | 2-Amino-5-methoxybenzoic acid is a general reagent used in the synthesis of substituted isoquinolinonaphthyridines, quinazolinones, imidazobenzodiazepines, pyridoquinazolones and polycyclic hexahydrobenzo[c]acridines. | | Definition | ChEBI: 2-Amino-5-methoxybenzoic acid is a methoxybenzoic acid. | | reaction suitability | reaction type: solution phase peptide synthesis | | Synthesis | Using 5-methoxy-2-nitrobenzoic acid (1) as starting material, its nitro group was reduced by catalytic hydrogenation using H2 and Pd/C to afford 2-amino-5-methoxybenzoic acid (2) in quantitative yield. Subsequently, compound (2) was subjected to diazotization reaction with NaNO2 followed by treatment with Na2S2 to obtain stable disulfide compound (3) in 80% yield. This disulfide (3) was directly reacted with SOCl2 without further purification, followed by reaction with 2-chloroethylamine in the presence of Et3N to produce amide (4) in 90% yield. The compound (4) was converted to the cyclized product (5) by a one-pot method with trimethylphosphine and Et3N co-refluxed in THF. Finally, reduction of the cyclized amide (5) using LiAlH4 afforded 7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine (6). | | References | [1] Patent: US2007/49572, 2007, A1. Location in patent: Page/Page column 34
[2] Patent: US2005/215540, 2005, A1. Location in patent: Page/Page column 37
[3] Patent: WO2016/23826, 2016, A1. Location in patent: Page/Page column 40
[4] Synthesis (Germany), 2017, vol. 49, # 1, p. 135 - 144
[5] Medicinal Chemistry Research, 2002, vol. 11, # 9, p. 504 - 537 |
| | 2-Amino-5-methoxybenzoic acid Preparation Products And Raw materials |
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