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Chemical Structure| 871101-87-0 Chemical Structure| 871101-87-0

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Chemical Structure| 871101-87-0

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Product Details of [ 871101-87-0 ]

CAS No. :871101-87-0
Formula : C15H15NO3
M.W : 257.28
SMILES Code : CC(C1=CC=C(OCC2=CC=CC=C2)C(N)=C1O)=O
MDL No. :MFCD20485008
InChI Key :DPDBWSYVDANFKH-UHFFFAOYSA-N
Pubchem ID :57989252

Safety of [ 871101-87-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 871101-87-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 871101-87-0 ]

[ 871101-87-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 871101-87-0 ]
  • [ 79-04-9 ]
  • [ 1035229-32-3 ]
YieldReaction ConditionsOperation in experiment
95% 2-Chloroacetyl chloride (1.77 mL) was added dropwise to a stirred mixture of 1-(3-amino-4-(benzyloxy)-2-hydroxyphenypethanone (5.20 g, 20.2 mmol) and sodium hydrogen carbonate (3.74 g, 44.5 mmol) in DMF (30 mL) and then stirred for a further two hours. Cesium carbonate (7.90 g, 24.2 mmol) was added and the mixture was heated at 100 C. for 20 hours. The mixture was cooled to room temperature, quenched with water (500 mL), extracted with ethyl acetate (2×200 mL), and the combined organic layers washed with water (3×300 mL) and brine. The organic layer was then dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The solid residue was treated with ether, filtered and the eluent dried to afford the title compound (5.70 g, 19.2 mmol, 95% yield) as a beige solid. MS (ESI+) 298 [M+H]+.
86% Intermediate 148-Acetyl-5-benzyloxy-4Af-benzo[1 ,4]oxazin-3-one; Chloroacetyl chloride (1.25 mL, 15.5 mmol) was added to a stirred mixture of 1-(3-amino-4-benzyloxy-2-hydroxy-phenyl)-ethanone (US2005/0277632) (3.63 g, 14.1 mmol) and NaHCO3 (2.69 g, 32.0 mmol) in dry DMF (20 mL). The reaction mixture was stirred at RT for 2 h. Caesium carbonate (5.53 g, 17.0 mmol) was added and the mixture was heated at 100 0C, protected from moisture, for 2.5 h. The reaction mixture was cooled to RT and poured into water (-300 mL) to afford a turbid, milky solution from which a solid precipitated. The solid was removed by vacuum filtration and taken up in EtOAc by sonication and the aqueous layer was extracted with EtOAc. The combined organic layers were further washed with water, brine, dried (MgSO4), and concentrated in vacuo Xo afford a dark brown solid. Yield: 3.60 g (86%). LC-MS (Method 3): Rt 3.24 min, m/z 298 [M+H]+.
Step iv) 8-Acetyl-5-(benzyloxy)-2H-benzo[b][l,4]oxazin-3(4H)-one2-Chloroacetyl chloride (1.771 mL) was added dropwise to a stirred mixture of l-(3- amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone (5.2 g) [Step iii] and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for a further 2 h. Cesium carbonate (7.90 g) was added and heated at 1000C for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2 x 200 mL), washed with water (3 x 300 mL) and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The solid residue was treated with ether, filtered and dried to afford the subtitled compound as a beige solid (5.7 g).1E NMR (399.826 MHz, DMSO) delta 10.33 (s, IH), 7.55 (m, 2H), 7.39 (m, 2H), 7.34 (d, J = 8.8 Hz, IH), 7.33 (m, IH), 6.89 (d, J = 9.2 Hz, IH), 5.27 (s, 2H), 4.67 (s, 2H), 3.32 (s 3H).
Step iv) 8-Acetyl-5-(benzyloxy)-2H-benzo[b][l,4]oxazin-3(4H)-one 2-Chloroacetyl chloride (1.77 mL) was added dropwise to a stirred mixture of l-(3-amino- 4-(benzyloxy)-2-hydroxyphenyl)ethanone (5.2 g) and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for a further 2 h. Cesium carbonate (7.90 g) was added and heated at 1000C for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2 x 200 mL), washed with water (3 x 300 mL) and brine, dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The solid residue was treated with ether, filtered and dried to afford the subtitled compound as a beige solid (5.7 g). <n="34"/>1H NMR (400 MHz, DMSO-d6) delta 10.33 (s, IH), 7.55 (m, 2H), 7.39 (m, 2H), 7.34 (d, J = 8.8 Hz, IH), 7.33 (m, IH), 6.89 (d, J = 9.2 Hz, IH), 5.27 (s, 2H), 4.67 (s, 2H), 3.32 (s, 3H).

  • 2
  • [ 871101-87-0 ]
  • [ 1035229-32-3 ]
 

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