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Chemical Structure| 194151-99-0 Chemical Structure| 194151-99-0

Structure of 194151-99-0

Chemical Structure| 194151-99-0

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Product Details of [ 194151-99-0 ]

CAS No. :194151-99-0
Formula : C9H11NO
M.W : 149.19
SMILES Code : OC1C2=C(N=CC=C2)CCC1
MDL No. :MFCD01312582

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Application In Synthesis of [ 194151-99-0 ]

* 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 [ 194151-99-0 ]

[ 194151-99-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 53400-41-2 ]
  • [ 194151-99-0 ]
YieldReaction ConditionsOperation in experiment
90.9% With sodium tetrahydroborate; In ethanol; at 25℃; for 16h; 7,8-dihydro-quinoline -5 (6H) - one (2.2g, 14.9mmol) was dissolved in ethanol (20 mL) was added NaBH4 (1.2g, 31.7mmol), 25 reaction was stirred for 16 hours. The reaction mixture was washed with water (30mL) was quenched by adding ethyl acetate (20mL × 3) organic phases spin dry to give the title compound as a white solid (2g, 90.9% yield).
With sodium tetrahydroborate; In methanol; ethyl acetate; Step 1. A stirred solution of (5,6,7,8)-tetrahydroquinoline-5-one (500 mg, 3.4 mmol) in MeOH (17 mL) was cooled to 0 C. under Argon and treated with NaBH4 (128.7 mg, 3.4 mmol). The reaction was stirred over 16 h and allowed to warm to ambient temperature. The solvent was removed under reduced pressure and the crude oil was chromatographed on a silica gel column packed in 95:5 EtOAc:hexanes and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure to give the 5-hydroxy-(5,6,7,8)-tetrahydroquinoline.
  • 2
  • [ 845305-83-1 ]
  • [ 194151-99-0 ]
  • [ 1138448-11-9 ]
YieldReaction ConditionsOperation in experiment
15% 5,6,7,8-Tetrahydroquinolin-5-ol (110 mg, 0.743 mmol) was dissolved in 6 mL of CH2Cl2 and the resulting solution was cooled to 0 0C. Triethylamine (0.26 mL, 1.87 mmol) <n="49"/>was then added followed by methanesulfonyl chloride (72 uL, 0.926 mmol) and the reaction was allowed to stir for about 2 hours at 0 0C, then stirred at room temperature for an additional 2 hours. The reaction mixture was then added dropwise to a stirred mixture of compound IB (200 mg, 0.703 mmol, available from Example 1 Step B) and triethylamine (0.3 mL, 2.15 mmol) in 5 mL OfCH2Cl2. The reaction was heated to reflux and allowed to stir at this temperature for about 15 hours. The reaction mixture was then cooled to RT, diluted with CH2Cl2 and the organic layer was washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo to provide a crude yellow oil. The crude oil was purified using preparative TLC (CH2Cl2 - MeOH = 25 :1, v/v) to provide 46 mg of compound 7A (15%) as a near colorless oil.
 

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