| Identification | Back Directory | [Name]
2-Methyl-1,3-benzoxazole-6-carboxylic acid | [CAS]
13452-14-7 | [Synonyms]
1,2-Ethanediamine,5-phenyl-
2-Methylbenzoxazole-6-carboxylic Acid
2-Methyl-6-benzoxazole carboxylic acid
6-Benzoxazolecarboxylic acid, 2-methyl-
2-METHYLBENZO[D]OXAZOLE-6-CARBOXYLIC ACID
2-Methyl-1,3-benzoxazole-6-carboxylic acid
Benzenepropanoicacid,7-methyl-β-oxo-,ethylester | [Molecular Formula]
C9H7NO3 | [MDL Number]
MFCD07787266 | [MOL File]
13452-14-7.mol | [Molecular Weight]
177.16 |
| Chemical Properties | Back Directory | [Melting point ]
>230°C (dec.) | [Boiling point ]
353.5±15.0 °C(Predicted) | [density ]
1.380±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly, Heated), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
3.68±0.30(Predicted) | [color ]
Pale Beige | [InChI]
1S/C9H7NO3/c1-5-10-7-3-2-6(9(11)12)4-8(7)13-5/h2-4H,1H3,(H,11,12) | [InChIKey]
GFYDDTFAVDJJAI-UHFFFAOYSA-N | [SMILES]
Cc1nc2ccc(cc2o1)C(O)=O |
| Hazard Information | Back Directory | [Uses]
2-Methyl-1,3-benzoxazole-6-carboxylic Acid is used in the synthesis of orexin 1 receptor antagonists, used in the treatment of obesity. Also used in the synthesis of novel benzoxazole amides as novel enhancers of HIV-1 protease inhibitors. | [Synthesis]
General procedure for the synthesis of 2-methyl-1,3-benzoxazole-6-carboxylic acid from methyl 2-methylbenzo[d]oxazole-6-carboxylate: To a mixed solution of tetrahydrofuran (THF) (300 mL) and water (H2O) (100 mL) of methyl 2-methyl-1,3-benzoxazole-6-carboxylate (8) (12.2 g, 0.064 mol), lithium hydroxide monohydrate (LiOH-H2O) (5.4 g, 0.128 mol) and the reaction mixture was stirred vigorously at room temperature. After 2 h of reaction, THF was removed by rotary evaporator under reduced pressure.The remaining aqueous phase was acidified with acetic acid (HOAc) to pH ≈ 3 and then extracted several times with dichloromethane (CH2Cl2). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated to give a beige solid product (10.2 g, 90% yield): melting point 245-246 °C (literature value 245-246 °C); thin-layer chromatography (TLC) (silica gel plate, unfolding agent ethyl acetate/methanol (90:10), detected under a UV lamp) showed a single spot with an Rf value of 0.38. Nuclear magnetic resonance hydrogen spectrum (1H NMR) (300 MHz, DMSO-d6): δ 2.66 (s, 3H, NCH3), 7.75 (d, J = 8.3 Hz, 1H, H-5), 7.96 (dd, J = 8.3, 1.4 Hz, 1H, H-4), 8.16 (d, J = 0.7 Hz, 1H, H-7), 13.12 (bs , 1H, OH). | [References]
[1] Patent: EP1782811, 2007, A1. Location in patent: Page/Page column 60
[2] Patent: EP1669348, 2006, A1. Location in patent: Page/Page column 68
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 21, p. 6661 - 6664
[4] Patent: WO2016/100184, 2016, A1. Location in patent: Paragraph 00323-00324
[5] Patent: US2007/160538, 2007, A1. Location in patent: Page/Page column 19-20 |
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