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[ CAS No. 69601-46-3 ] {[proInfo.proName]}

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Chemical Structure| 69601-46-3
Chemical Structure| 69601-46-3
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Product Details of [ 69601-46-3 ]

CAS No. :69601-46-3 MDL No. :
Formula : C10H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 177.20 Pubchem ID :-
Synonyms :

Safety of [ 69601-46-3 ]

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Application In Synthesis of [ 69601-46-3 ]

* 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 [ 69601-46-3 ]

[ 69601-46-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 75-30-9 ]
  • [ 69601-46-3 ]
  • [ 187679-65-8 ]
YieldReaction ConditionsOperation in experiment
88% With caesium carbonate; In acetone; at 55.0℃; for 3.0h; To a stirred solution of compound 22 (350 mg, 1.98 mmol) and 2-iodopropane (0.590 ml, 5.93 mmol) in acetone (16 ml) was added Cs2CO3 (2.90 g, 8.91 mmol), and heated at 55C for 3h. The mixture was filtered over Celite and washed with acetone. The filtrate was concentrated to give crude compound 23. This was diluted with ethyl acetate, washed with water and sat. NaCl aq, dried (MgSO4), and concentrated. This was purified by SiO2 chromatography to give compound 23 (382 mg, 88%) as a colorless oil. 1H-NMR (270MHz) delta (CDCl3) 6.88 (1 H, d, J = 8.4 Hz), 6.80-6.70 (m, 2H), 4.49 (1H, hep, J = 5.9 Hz), 3.33 (3H, s), 2.86 (2H, t, J = 7.2 Hz), 2.66-2.59 (2H, m), 1.33 (6H, d, J = 5.9 Hz) ppm.
With caesium carbonate; In acetone; (ii). 6-Isopropoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 23) To a stirred solution of compound 22 (350 mg, 1.98 mmol) and 2-iodopropane (0.590 ml, 5.93 mmol) in acetone (16 ml) was added Cs2CO3 (2.90 g, 8.91 mmol), and heated at 55 C. for 3 h. The mixture was filtered over Celite and washed with acetone. The filtrate was concentrated to give crude compound 23. This was diluted with ethyl acetate, washed with water and sat. NaCl aq, dried (MgSO4), and concentrated. This was purified by SiO2 chromatography to give compound 23 (382 mg, 88%) as a colorless oil. 1H-NMR (270 MHz) delta (CDCl3) 6.88 (1H, d, J=8.4 Hz), 6.80-6.70 (m, 2H), 4.49 (1H, hep, J=5.9 Hz), 3.33 (3H, s), 2.86 (2H, t, J=7.2 Hz), 2.66-2.59 (2H, m), 1.33 (6H, d, J=5.9 Hz) ppm.
With caesium carbonate; In acetone; (ii) 6-Isopropoxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 23) To a stirred solution of compound 22 (350 mg, 1.98 mmol) and 2-iodopropane (0.590 ml, 5.93 mmol) in acetone (16 ml) was added Cs2CO3 (2.90 g, 8.91 mmol), and heated at 55 C. for 3h. The mixture was filtered over celite and washed with acetone. The filtrate was concentrated to give crude compound 23. This was diluted with AcOEt, washed with water and sat. NaCl aq, dried (MgSO4), and concentrated. This was purified by SiO2 chromatography to give compound 23 (382 mg, 88%) as a colorless oil. 1H-NMR (270 MHz) delta (CDCl3) 6.88 (1H, d, J 8.4 Hz), 6.80-6.70 (m, 2H), 4.49 (1H, hep, J=5.9 Hz), 3.33 (3H, s), 2.86 (2H, t, J=7.2 Hz), 2.66-2.59 (2H, m), 1.33 (6H, d, J=5.9 Hz) ppm.
  • 2
  • [ 187679-62-5 ]
  • [ 69601-46-3 ]
YieldReaction ConditionsOperation in experiment
76% With boron tribromide; In dichloromethane; (i) 6-Hydroxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 22) To a stirred solution of compound 15 (500 mg, 2.61 mmol) in CH2Cl2 (7 ml) was added BBr3 (1.0M in CH2Cl2, 5.74 ml, 5.74 mmol) at room temperature, and stirred for 3h. The mixture was poured into ice water. The aqueous layer was extracted with AcOEt (*2). The combined organic layers were washed with sat. NaCl aq, dried (MgSO4), filtered, and concentrated to give compound 22 (350 mg, 76%) as a colorless crystal. 1H-NMR (270 MHz) delta (CDCl3) 6.85 (1H, d, J=8.4 Hz), 6.75-6.70 (m, 2H), 3.34 (3H, s), 2.86 (2H, t, J=7.1 Hz), 2.63 (2H, t, J=7.1 Hz) ppm.
76% With boron tribromide; In dichloromethane; at 20.0℃; for 3.0h; To a stirred solution of compound 15 (500 mg, 2.61mmol) in CH2Cl2 (7 ml) was added BBr3 (1.0 M in CH2Cl2, 5.74 ml, 5.74 mmol) at room temperature, and stirred for 3h. The mixture was poured into ice water. The aqueous layer was extracted with ethyl acetate (x 2). The combined organic layers were washed with sat. NaCl aq, dried (MgSO4), filtered, and concentrated to give compound 22 (350 mg, 76%) as a colorless crystal. 1H-NMR (270MHz) delta (CDCl3) 6.85 (1H, d, J = 8.4 Hz), 6.75-6.70 (m, 2H), 3.34 (3H, s), 2.86 (2H, t, J = 7.1 Hz), 2.63 (2H, t, J = 7.1 Hz) ppm.
YieldReaction ConditionsOperation in experiment
76% (i). 6-Hydroxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline (Compound 22) To a stirred solution of compound 15 (500 mg, 2.61 mmol) in CH2Cl2 (7 ml) was added BBr3 (1.0 M in CH2Cl2, 5.74 ml, 5.74 mmol) at room temperature, and stirred for 3 h. The mixture was poured into ice water. The aqueous layer was extracted with ethyl acetate (x 2). The combined organic layers were washed with sat. NaCl aq, dried (MgSO4), filtered, and concentrated to give compound 22 (350 mg, 76%) as a colorless crystal. 1H-NMR (270 MHz) 6 (CDCl3) 6.85 (1H, d, J=8.4 Hz), 6.75-6.70 (m, 2H), 3.34 (3H, s), 2.86 (2H, t, J=7.1 Hz), 2.63 (2H, t, J=7.1 Hz) ppm.
  • 4
  • [ 69601-46-3 ]
  • [ 123724-40-3 ]
  • [ 368834-28-0 ]
YieldReaction ConditionsOperation in experiment
17% silver carbonate; In toluene; PREPARATION 35 1-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-one To a dry toluene solution of [1-Iodo-cyclopropylsulfanyl]-benzene (375 mg, 1.36 mmol) was added <strong>[69601-46-3]6-Hydroxy-1-methyl-3,4-dihydro-1H-quinolin-2-one</strong> (200 mg, 1.13 mmol) and silver carbonate (312 mg, 1.13 mmol) under nitrogen and the reaction mixture was heated to 55 C. It took 3 more additions of the reagents to take the reaction to completion. The reaction was cooled to room temperature, filtered to remove the silver iodide and concentrated under vacuum to yield crude material. This was flash chromatograhed using 30% ethyl acetate/hexane to yield the title compound as a viscous oil (64 mg, 17% yield). 1H NMR (400 MHz, CDCl3) delta1.31-1.33 (2H, m), 1.41-1.43 (2H, m), 2.59-2.62 (2H, m), 2.83-2.87 (2H, m), 3.31 (3H, s), 6.86-6.98 (4H, m), 7.20-7.31 (2H, m), 7.44-7.47 (2H, m). m/z (APCI+) 326 (M+1). HPLC (aqueous 200 Mm ammonium acetate buffer/ acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 muM, 125*4 mm column), 6.59 minutes.
  • 5
  • [ 69601-46-3 ]
  • [ 75-03-6 ]
  • [ 368834-35-9 ]
YieldReaction ConditionsOperation in experiment
33% In tetrahydrofuran; PREPARATION 38 6-Ethoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one 1.0M potassium t-butoxide/THF (5.65 ml, 5.65 mmol) was added to <strong>[69601-46-3]6-Hydroxy-1-methyl-3,4-dihydro-1H-quinolin-2-one</strong> (200 mg, 1.13 mmol) followed by the addition of ethyl iodide (452 mul, 5.65 mmol). The reaction mixture was stirred at room temperature for 2 hours and heated to 45 C. for an overnight. The salts were filtered off, rinsed with ethyl acetate and the combined filtrate was concentrated down to a residue. This was chromatographed using 1:1 ethylacetate/hexane to yield the title compound as a white solid (76 mg, 33% yield). 1H NMR (400 MHz, CDCl3) delta1.36 (3H, t, J=6.9 Hz), 2.58 (2H, m), 2.82 (2H, m), 3.29 (3H, s), 3.96 (2H, q, J=7.0 Hz), 6.71 (2H, m), 6.84 (1H, d, J=8.7 Hz). m/z (APCI+) 206 (M+1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 muM, 125*4 mm column), 4.453 min.
  • 6
  • BBr3/CH2Cl2 [ No CAS ]
  • [ 187679-62-5 ]
  • [ 69601-46-3 ]
YieldReaction ConditionsOperation in experiment
84% In dichloromethane; PREPARATION 34 6-Hydroxy-1-methyl-3,4-dihydro-1H-quinolin-2-one 5.74 ml of 1.0 M BBr3/CH2Cl2 solution was added to a dry CH2Cl2 solution of <strong>[187679-62-5]6-methoxy-1-methyl-3,4-dihydro-1H-quinolin-2-one</strong> (500 mg, 2.62 mmol) under nitrogen. The reaction mixture was stirred for 2 hours, poured into ice water and extracted with ethyl acetate (150 ml). The combined organic extract was washed with brine,dried (MgSO4) and the solvent was evaporated under reduced pressure to yield the title compound as a pink solid (392 mg, 84%). 1H NMR (400 MHz, CD3OD) delta2.52-2.56 (2H, m), 2.77-2.81 (2H, m), 3.28 (3H,s), 6.62-6.67 (2H, m), 6.92 (1H, d, J=8.72 Hz). m/z (APCI-) 176 (M-1). HPLC (aqueous 200 Mm ammonium acetate buffer/acetonitrile gradient, 3.0 ml/min, Hewlett Packard ODS Hypersil 5 muM, 125*4 mm column), 2.51 minutes.
  • 7
  • [ 187679-63-6 ]
  • [ 69601-46-3 ]
  • [ 187679-72-7 ]
YieldReaction ConditionsOperation in experiment
(i) <strong>[69601-46-3]6-Hydroxy-1-methyl-2-oxo-1,2,3,4-tetrahydroquinoline</strong>-7-carboxaldehyde (Compound 34) This compound was prepared from compound 16 in the same manner of compound 22. 1H-NMR (270 MHz) delta (CDCl3) 10.89 (1H, s), 9.88 (1H, s), 7.07 (1H. s), 6.85 (1H, s), 3.39 (3H, s), 2.98-2.88 (2H, m), 2.68-2.58 (2H, m) ppm.
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