| Identification | Back Directory | [Name]
Benzoic acid, 4-amino-5-cyano-2-hydroxy-3-methyl- (9CI) | [CAS]
72817-94-8 | [Synonyms]
4-Amino-5-cyano-2-hydroxy-3-methylbenzoic acid
Benzoic acid, 4-aMino-5-cyano-2-hydroxy-3-Methyl-
Benzoic acid, 4-amino-5-cyano-2-hydroxy-3-methyl- (9CI) | [Molecular Formula]
C9H8N2O3 | [MOL File]
72817-94-8.mol | [Molecular Weight]
192.17 |
| Chemical Properties | Back Directory | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [InChI]
InChI=1S/C9H8N2O3/c1-4-7(11)5(3-10)2-6(8(4)12)9(13)14/h2,12H,11H2,1H3,(H,13,14) | [InChIKey]
PMIRQABZZUUPJI-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C1=CC(C#N)=C(N)C(C)=C1O |
| Hazard Information | Back Directory | [Synthesis]
Step B: Synthesis of 4-amino-5-cyano-2-hydroxy-3-methylbenzoic acid; LiOH-H2O (8.4 g, 0.2 mol) was dissolved in a mixed solvent of ethanol/water (1:1, 300 mL) at room temperature, followed by addition of ethyl 4-amino-5-cyano-2-hydroxy-3-methylbenzoate (22 g, 0.1 mol). The reaction mixture was heated to 80 °C and refluxed for 4 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the residue was diluted with 100 mL of water and washed with petroleum ether/ethyl acetate (1:1, 2 x 200 mL). The aqueous layer was separated and the pH was adjusted to 5 with 1.5 N HCl and the precipitated solid product was collected by filtration. The aqueous layer was further extracted with ethyl acetate (2 × 300 mL), the organic phases were combined, dried and concentrated to give additional product. All products were combined and washed with petroleum ether solution of 5% ethyl acetate to give pure target compound (19 g, yield >95%).TLC detection conditions: methanol/chloroform (1:4), Rf=0.2. | [References]
[1] Patent: WO2007/14926, 2007, A1. Location in patent: Page/Page column 127
[2] Patent: US2009/118312, 2009, A1. Location in patent: Page/Page column 53
[3] Liebigs Annalen der Chemie, 1979, p. 2005 - 2010 |
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