| Identification | More | [Name]
METHYL 4-AMINOSALICYLATE | [CAS]
4136-97-4 | [Synonyms]
METHYL 4-AMINO-2-HYDROXYBENZENECARBOXYLATE
METHYL 4-AMINO-2-HYDROXYBENZOATE
METHYL 4-AMINOSALICYLATE
P-AMINO METHYL SALICYLATE
4-amino-2-hydroxy-benzoicacimethylester
amino-salicylicacimethylester
methylp-aminosalicylate
p-aminosalicylicacidmethylester
pasmethylester
4-Aminosalicylic Acid Methyl Ester
4-AMINOSALICYLICMETHYLESTER
4-AMINOSALICYLIC ACID ESTER
2-Hydroxy-4-aminobenzoic acid methyl ester
4-Amino-2-hydroxybenzoic acid methyl ester | [EINECS(EC#)]
223-958-3 | [Molecular Formula]
C8H9NO3 | [MDL Number]
MFCD00088091 | [Molecular Weight]
167.16 | [MOL File]
4136-97-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
120-123°C | [Boiling point ]
120 °C | [density ]
1.305±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
9.81±0.10(Predicted) | [color ]
White to Pale Beige | [Water Solubility ]
Slightly soluble in water. | [λmax]
254nm(lit.) | [CAS DataBase Reference]
4136-97-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Methyl 4-aminosalicylate is used as pharmaceutical intermediate. | [Definition]
ChEBI: P-Aminosalicylic acid methyl ester is an aromatic amine. | [Synthesis]
Step 2: Preparation of methyl 4-amino-2-hydroxybenzoate
In a 500 mL Parr reactor, methyl 2-hydroxy-4-nitrobenzoate (1.3 g, 6.59 mmol) was mixed with a suspension formed by 10% Pd/C catalyst (100 mg) in methanol (40 mL). The reaction mixture was shaken for 1 h under hydrogen atmosphere (30 psi). Upon completion of the reaction, the catalyst was removed by filtration through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. Methyl 4-amino-2-hydroxybenzoate was obtained as a yellow solid (1.08 g, 6.46 mmol, 98% yield). The product was analyzed by UPLC-MS showing 100% purity and the mass spectrum (MS/ESI+) showed a molecular ion peak [MH]+ of 167.9. | [References]
[1] ACS Catalysis, 2014, vol. 4, # 6, p. 1777 - 1782
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 20, p. 3597 - 3600
[3] Patent: US2014/155391, 2014, A1. Location in patent: Paragraph 0432; 0434
[4] Journal of the Chemical Society, 1949, p. 1498,1502
[5] Proceedings - Indian Academy of Sciences, Section A, 1950, vol. 32, p. 357,362 |
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