| Identification | Back Directory | [Name]
2(3H)-Benzoxazolone,7-amino-(9CI) | [CAS]
81282-60-2 | [Synonyms]
7-Amino-2-benzoxazolone
7-Amino-2-benzoxazolinone
7-amino-3h-1,3-benzoxazol-2-one
7-Aminobenzo[d]oxazol-2(3H)-one
7-Amino-1,3-benzoxazol-2(3H)-one
2(3H)-Benzoxazolone,7-amino-(9CI)
7-Amino-2,3-dihydro-2-oxo-1,3-benzoxazole | [EINECS(EC#)]
462-910-8 | [Molecular Formula]
C7H6N2O2 | [MDL Number]
MFCD09753616 | [MOL File]
81282-60-2.mol | [Molecular Weight]
150.13 |
| Chemical Properties | Back Directory | [Appearance]
Tan Solid | [density ]
1.438±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [solubility ]
soluble in Acetone, Chloroform, Ethyl Acetate, Methanol | [form ]
powder to crystal | [pka]
9.06±0.70(Predicted) | [color ]
White to Yellow to Orange |
| Hazard Information | Back Directory | [Chemical Properties]
Tan Solid | [Uses]
Intermediate for the preparation of bifeprunox mesylate | [Synthesis]
General procedure for the synthesis of 7-amino-2(3H)-benzoxazolone from 5-chloro-7-nitrobenzo[d]oxazol-2(3H)-one: Compound 6 (4 g, 18.56 mmol) was dissolved in a 4:1 MeOH/DMF solvent mixture (50 ml) and 10% Pd/C catalyst (500 mg) was added. The hydrogenation reaction was carried out at 60 psi hydrogen pressure overnight. The progress of the reaction was monitored by TLC (unfolding agent ratio ethyl acetate:petroleum ether = 3:7). After completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated under vacuum. The crude product was crystallized with ether to give 2.8 g of beige solid in 99% yield. The structure of the product was confirmed by 1HNMR (DMSO-d6, 200 MHz): δ5.31 (2H, bs, NH2), 6.26 (1H, dd, J = 7.6 Hz, J'= 1 Hz, Ar-H), 6.38 (1H, dd, J = 8.4 Hz, J'= 1.2 Hz, Ar-H), 6.80 (1H, t, J = 8 Hz, Ar-H), 11.32 (1H, bs, NH). | [References]
[1] Patent: EP2377850, 2011, A1. Location in patent: Page/Page column 22
[2] Patent: US2006/194812, 2006, A1. Location in patent: Page/Page column 6
[3] Patent: WO2005/16898, 2005, A2. Location in patent: Page/Page column 11
[4] Patent: US2006/40932, 2006, A1. Location in patent: Page/Page column 5
[5] Patent: US2010/119622, 2010, A1. Location in patent: Page/Page column 17 |
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