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Chemical Structure| 61703-95-5 Chemical Structure| 61703-95-5

Structure of 61703-95-5

Chemical Structure| 61703-95-5

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Product Details of [ 61703-95-5 ]

CAS No. :61703-95-5
Formula : C11H11NO
M.W : 173.21
SMILES Code : CC1C2C(=C(C=CC=2)OC)N=CC=1

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Application In Synthesis of [ 61703-95-5 ]

* 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 [ 61703-95-5 ]

[ 61703-95-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 61703-95-5 ]
  • [ 3846-73-9 ]
YieldReaction ConditionsOperation in experiment
[1805] Into a 100 mL round bottom flask containing a stirring bar and fitted with a reflux condenser and a septum was placed 10 mL 70% sulfuric acid, sodium iodide (0.23 g, 0.24 mmol) and anisidine (2.96 g, 24 mmol). This mixture was heated to 110 C., and to it was added methyl vinyl ketone (3.2 mL, 38.45 mmol) slowly over 5 hours via a syringe pump. After heating an additional hour, the reaction was cooled and poured into 50 mL 1M aqueous Na2CO3 and extracted with CH2Cl2. The combined organic extracts were extracted with 12M HCl. The acidic extracts were neutralized with 6M NaOH and extracted with CH2Cl2. The combined organic extracts were washed with water, brine dried over Na2SO4, filtered and the solvent removed. The residue was dissolved in EtOAc and passed through a silica pad to get the methyl ether, which was dissolved in 50 mL HBr and heated to reflux for 30 hours, after which the reaction was cooled and neutralized with 1ON NaOH and extracted with CH2Cl2. The combined organic extracts were combined, washed with water, brine, dried over Na2SO4, filtered and the solvent removed in vacuo to give 4-methylquinolin-8-ol. [1806] 1H NMR (CDCl3) delta: 2.70(3H, s); 7.18(1H, t, j=4Hz); 7.27(1H, d, j=4.2 Hz); 7.47(1H, d, j=4Hz); 8.63(1H, d,j=4.2 Hz) ES MS M+1=160
  • 2
  • [ 3846-73-9 ]
  • [ 74-88-4 ]
  • [ 61703-95-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetone; at 20℃; for 8.0h; The intermediate INT 1 was synthesized through ring closure from 2-aminophenol reacted with methyl vinyl ketone. INT 1 was reacted with various alkyl halides to afford 8-alkoxy-4methylquinoline derivatives as intermediates. Corresponding Rr(CH2)_,OH was reacted with intermediates to synthesize series of compounds J and I. The protective group J was removed by hydrogenation (method illustrated in example 1) to obtain compound K.
With potassium carbonate; In acetone; at 20℃; for 8.0h; Example 7 - Preparation of 8-hydroxyquino -yi) or (S-alkovyquino -yl) aikyl alcohols SWT 1 11 = 11-12 n = 11-12 K1 - K2 J1 - J2 Reagents and conditions: (a) methyl vinyl ketone, HCL reflux, (b) Mel. sCCh, acetone, rt 8h; Elf or 2~bromopropane or methylenecyclopropyl bromide, K2CO3, DMF, 60 6C, (c) I) LH.MDS, THF, 0 C, 1 h.: 2) Br(CH2)..i H, rt. (d) BnBr. KOM, EtOH, reflux, (e) H FontWeight="Bold" FontSize="10" Pd/C, MeOH, rt 24 h. Method: Te intermediate INT was synthesized through ring closure from 2-arninophenol reacted with methyl vin l ketone. INT I was reacled with various aJkyl halides to afford 8-alkoxy- 4methylquino.)me derivatives as intermediates. Corresponding Brt'CHs iOH was reacted with intermediates to synthesize series of compounds 3 and I. The protective group J was removed by hydrogenaiiori (method iliustraied in example I) to obtain compound K. 1 1 -(S-nietlioxyquinoIin-4-yl)imde?aii-i-oI ( I) YD: 34%. lH NMR (400 MHz, CDt) 88.80 (ckt J - 4.4, 0.6 Hz. IH), 7.59 (dd, J ~ 8.4, 0.8 Hz, I H), 7.44-7.49 (m, 1H 7.03 (d. J - 7.6 Hz, Hh 4.08 (3, 3H); 3.63 ( J ::: 6.8 Hz, 2H), 3.03 (t J - 7.6 Hz, 2H), 1.74 (quia - 7.6 Hz, 2H), S .55 (quin, J - 7.2 Hz, 2H), 1.23-1.45 (br, 1SH); MS. m/z 329.9, JM+Hf .
 

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