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Chemical Structure| 422312-00-3 Chemical Structure| 422312-00-3

Structure of 422312-00-3

Chemical Structure| 422312-00-3

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Product Details of [ 422312-00-3 ]

CAS No. :422312-00-3
Formula : C12H11NO2
M.W : 201.22
SMILES Code : O=C(C1=CC=CC2=C1NC3=C2CCC3)O
MDL No. :MFCD09863427

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Application In Synthesis of [ 422312-00-3 ]

* 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 [ 422312-00-3 ]

[ 422312-00-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 33906-30-8 ]
  • [ 120-92-3 ]
  • [ 422312-00-3 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; In ethanol; for 4.5h;Heating / reflux; 2-hydrazinobezoic acid hydrochloride (3.44 g, 18.23 mmol) and cyclopentanone (2.0 ml, 21.88 mmol) was refluxed in EtOH (30 ml) and conc. H2SO4 (3 ml) for 4 h. Conc. H2SO4 (2 ml) was added and the mixture refluxed for 30 min more. Water and ET20 was added and organic phase washed with 1 M NaOH. The product was purified by flash chromatography. Yield 0.59 g (14%,No.70% pure). 'H NMR (400 MHz, CDC13) 8 1.44 (t, J = 7 Hz, 3 H), 2.55 (M, 2 H), 2.82-2. 92 (M, 4 H), 4.41 (q, J = 7 Hz, 2 H), 7.08 (t, J = 8 Hz, 1 H), 7.62 (d, J = 8 Hz, 1 H), 7. 78 (d, J = 8 Hz, 1 H). The crude material was dissolved in DMSO (5 ml) and KOH (500 mg) was added and the mixture stirred for 5 min. Benzyl bromide (500 TTL, 4.21 mmol) was added and the mixture stirred for 10 min before quenched with sat. NH4CL and extracted with Et2O. The organic phase was dried (MGS04) and the product was purified by flash chromatography using 2% EtOAc in hexanes. Yield 509 mg (68% pure (GC) ). The crude mixture was hydrolyzed using KOH (0.91 g) in refluxing EtOH (20 ml) and H20 (2 ml). After 1.5 h most OF ETOH was evaporated and the solution acidified by addition OF 2 M HC1. The precipitate was filtered washed with water and dried under vacuum. Yield 220 mg; white solid. Mp. 213 OC. 'H NMR (400 MHz, DMSO-d6) 8 2.81-2. 84 (M, 4 H), 3.29 (s, 2 H), 5.54 (s, 2 H), 6.82 (d, J=7 Hz, 2 H), 7.02 (t, J=8 Hz, 1 H), 7.15-7. 22 (M, 3 H), 7.37 (d, J=7 Hz, 1 H), 7.55 (d, J=8 Hz, 1 H), 12.78 (s, 1 H). 13C NMR (100 MHz, DMSO-d6) 6 24.47, 25.37, 27.74, 49.89, 118.11, 118.33, 122.27, 122.88, 126.45, 126.77, 127.09, 128.58, 137.03, 138.73, 149. 29, 168.84. MS: 292 (M+1). Found: C, 77.04 ; H, 5.63 ; N, 4.58%. Calc. for CLGHL7NO2 L/4H2O : C, 77.12 ; H, 5.96 ; N, 4.74%.
 

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