| Identification | Back Directory | [Name]
methyl 2-amino-5-hydroxybenzoate | [CAS]
1882-72-0 | [Synonyms]
Methyl 5-Hydroxyanthranilate
methyl 2-amino-5-hydroxybenzoate
5-Hydroxyanthranilic Acid Methyl Ester
4-hydroxy-2-(Methoxycarbonyl)benzenaMine
2-AMino-5-hydroxy-benzoic acid Methyl ester
Benzoic acid, 2-amino-5-hydroxy-, methyl ester | [Molecular Formula]
C8H9NO3 | [MDL Number]
MFCD05863263 | [MOL File]
1882-72-0.mol | [Molecular Weight]
167.163 |
| Chemical Properties | Back Directory | [Melting point ]
158.0 to 162.0 °C | [Boiling point ]
357.4±27.0 °C(Predicted) | [density ]
1.305±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
slightly sol. in Methanol | [form ]
powder to crystal | [pka]
9.41±0.18(Predicted) | [color ]
Light yellow to Brown |
| Hazard Information | Back Directory | [Synthesis]
Example 7:1-7:2 (Method F)
Step 1: 2-Amino-5-hydroxybenzoic acid (100 g, 0.653 mol) was dissolved in methanol (2 L) and concentrated sulfuric acid (100 mL, 100%) was added slowly. The reaction mixture was heated to reflux for 48 hours. After the reaction was completed, it was cooled to room temperature and neutralized with solid sodium bicarbonate to neutral. The reaction mixture was concentrated under reduced pressure, water (1.5 L) was added and the pH was adjusted with solid sodium bicarbonate to about 8. The precipitated solid was collected by filtration, washed with cold water and dried to give methyl 2-amino-5-hydroxybenzoate. Yield: 94 g (86% yield). | [References]
[1] Angewandte Chemie - International Edition, 2016, vol. 55, # 41, p. 12643 - 12649
[2] Angew. Chem., 2016, vol. 128, p. 12833 - 12839,7
[3] Journal of Organic Chemistry, 2001, vol. 66, # 8, p. 2784 - 2788
[4] Synlett, 2004, # 9, p. 1625 - 1627
[5] Patent: WO2009/127822, 2009, A2. Location in patent: Page/Page column 87 |
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