Alternatived Products of [ 13691-26-4 ]
Product Details of [ 13691-26-4 ]
CAS No. : 13691-26-4
MDL No. : MFCD00138492
Formula :
C10 H10 N2 O3
Boiling Point : -
Linear Structure Formula : -
InChI Key : YYYMDBUHBOEDTC-UHFFFAOYSA-N
M.W :
206.20
Pubchem ID : 299328
Synonyms :
Calculated chemistry of [ 13691-26-4 ]
Physicochemical Properties
Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.11
TPSA : 66.13 Ų
Pharmacokinetics
GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.73 cm/s
Lipophilicity
Log Po/w (iLOGP) : 1.7
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 1.48
Log Po/w (SILICOS-IT) : -0.23
Consensus Log Po/w : 1.09
Druglikeness
Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55
Water Solubility
Log S (ESOL) : -2.02
Solubility : 1.97 mg/ml ; 0.00956 mol/l
Class : Soluble
Log S (Ali) : -2.15
Solubility : 1.45 mg/ml ; 0.00701 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.12
Solubility : 1.57 mg/ml ; 0.00762 mol/l
Class : Soluble
Medicinal Chemistry
PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56
Application In Synthesis of [ 13691-26-4 ]
* 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 [ 13691-26-4 ]
1
[ 4641-57-0 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
90%
With sulfuric acid; nitric acid at 0℃; for 0.25h;
With sulfuric acid; nitric acid
With mixed acid
Reference：
[1]Kepiro, Miklos; Varkuti, Boglarka H.; Vegner, Laszlo; Voeroes, Gergely; Hegyi, Gyoergy; Varga, Mate; Malnasi-Csizmadia, Andras
[Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8211 - 8215][Angew. Chem., 2014, vol. 126, # 31, p. 8350 - 8354]
[2]Reppe et al.
[Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,204]
[3]Abdallah, Jassim M.; Moodie, Roy B.
[Journal of the Chemical Society. Perkin transactions II, 1983, p. 1243 - 1250]
2
[ 13691-26-4 ]
[ 13691-22-0 ]
Yield Reaction Conditions Operation in experiment
92%
With water at 20℃; Inert atmosphere; chemoselective reaction;
With methanol; nickel-chromium oxide at 80℃; Hydrogenation;
Reference：
[1]Dey, Raju; Mukherjee, Nirmalya; Ahammed, Sabir; Ranu, Brindaban C.
[Chemical Communications, 2012, vol. 48, # 64, p. 7982 - 7984]
[2]Reppe et al.
[Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,204]
3
[ 13691-26-4 ]
[ 87962-89-8 ]
Yield Reaction Conditions Operation in experiment
With barium dihydroxide
With sodium hydroxide at 50℃;
With sodium hydroxide In water
Reference：
[1]Reppe et al.
[Justus Liebigs Annalen der Chemie, 1955, vol. 596, p. 1,216]
[2]Abdallah, Jassim M.; Moodie, Roy B.
[Journal of the Chemical Society. Perkin transactions II, 1983, p. 1243 - 1250]
[3]Sedlak, Milos; Hejtmankova, Ludmila; Kasparova, Pavla; Kavalek, Jaromir
[Journal of Physical Organic Chemistry, 2002, vol. 15, # 3, p. 165 - 173]
4
[ 13691-26-4 ]
[ 87962-93-4 ]
Yield Reaction Conditions Operation in experiment
With mixed acid
5
[ 13691-26-4 ]
[ 87962-89-8 ]
C10 H12 N2 O3 (18) O
[ No CAS ]
C10 H12 N2 O3 (18) O
[ No CAS ]
C10 H10 N2 O2 (18) O
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride at 50℃; different temperatures and HCl concentrations; investagation of (18) O exchane with H2 (18) O;
6
[ 13691-26-4 ]
[ 58973-27-6 ]
Yield Reaction Conditions Operation in experiment
97%
With Lawessons reagent In tetrahydrofuran for 24h; Heating;
96%
With tetraphosphorus decasulfide In benzene Heating;
Reference：
[1]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
[2]Michael,J.P.; Hosken,G.D.; Howard,A.S.
[Tetrahedron, 1988, vol. 44, p. 3025]
7
4-Hydroxybutyryl-p-nitroanilid
[ No CAS ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
for 2h; Heating;
8
[ 87962-89-8 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; potassium chloride at 50℃; -ΔH0 ; -ΔS0 ; different temperatures and HCl concentrations; hydrogen isotope effect;
9
5-Methoxycarbonylmethylsulfanyl-1-(4-nitro-phenyl)-3,4-dihydro-2H-pyrrolium; bromide
[ No CAS ]
[ 13691-26-4 ]
[ 116614-83-6 ]
Yield Reaction Conditions Operation in experiment
With triethylamine; triphenylphosphine In dichloromethane for 2h; Ambient temperature; Yield given. Yields of byproduct given;
Yield Reaction Conditions Operation in experiment
alk. Hydrolyse (Kinetik): k (Tab.6);
Rk. mit Phenol;
Rk. mit Phenol: ΔH0 ; ΔS0 ;
Yield Reaction Conditions Operation in experiment
p-Nitroanilin, Butyrolacton;
4-Nitroanilin, γ-Butyrolacton, H2SO4;
entspr. Anilin (9, R=NO2), -Ozonisierung;
entspr. Stammverb., HNO3;
entspr. Amin, entspr. Lacton, Sulfanilsaeure;
12
[ 82547-19-1 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
With sodium hydroxide In methanol; water at 25℃;
13
[ 14372-12-4 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
68%
With carbon tetrabromide; triphenylphosphine In acetonitrile at 60℃; for 3h;
With aluminum oxide; ammonium iodide at 200℃; for 0.5h; Microwave irradiation;
Reference：
[1]Yang, Yong-Hua; Shi, Min
[Journal of Organic Chemistry, 2005, vol. 70, # 21, p. 8645 - 8648]
[2]Lebedev, A. T.; Mazur, D. M.; Kudelin, A. I.; Fedotov, A. N.; Gloriozov, I. P.; Ustynyuk, Yu. A.; Artaev, V. B.
[Rapid Communications in Mass Spectrometry, 2016, p. 2416 - 2422]
14
[ 358-23-6 ]
[ 13691-26-4 ]
C11 H10 F3 N2 O5 S(1+) *CF3 O3 S(1-)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
In dichloromethane at 20℃; for 0.5h;
15
C17 H17 N2 O2 S(1+) *CF3 O3 S(1-)
[ No CAS ]
C17 H18 N2 O3 S
[ No CAS ]
[ 909553-99-7 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
With hydrogen sulfide In N,N-dimethyl-formamide at 20℃; for 0.25h; Title compound not separated from byproducts.;
16
[ 13691-26-4 ]
C11 H13 N2 O2 S(1+) *CF3 O3 S(1-)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 0.25 h / 20 °C
17
[ 13691-26-4 ]
C12 H15 N2 O2 S(1+) *CF3 O3 S(1-)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 0.25 h / 20 °C
18
[ 13691-26-4 ]
methyl 4-[(4'-nitrophenyl)amino]butanedithioate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 0.25 h / 20 °C
3: H2 S / dimethylformamide / 0.25 h / 20 °C
19
[ 13691-26-4 ]
C11 H14 N2 O3 S
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 0.25 h / 20 °C
3: H2 S / dimethylformamide / 0.25 h / 20 °C
20
[ 13691-26-4 ]
ethyl 4-[(4'-nitrophenyl)amino]butanedithioate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 0.25 h / 20 °C
3: H2 S / dimethylformamide / 0.25 h / 20 °C
21
[ 13691-26-4 ]
C12 H16 N2 O3 S
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 0.25 h / 20 °C
3: H2 S / dimethylformamide / 0.25 h / 20 °C
22
[ 13691-26-4 ]
C17 H17 N2 O2 S(1+) *CF3 O3 S(1-)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: CH2 Cl2 / 0.5 h / 20 °C
2: 2,6-di-t-butylpyridine / CH2 Cl2 / 0.5 h
Multi-step reaction with 2 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 20 °C
Reference：
[1]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
[2]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
23
[ 13691-26-4 ]
[ 909553-99-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: CH2 Cl2 / 0.5 h / 20 °C
2: 2,6-di-t-butylpyridine / CH2 Cl2 / 0.5 h
3: H2 S / dimethylformamide / 0.25 h
Multi-step reaction with 3 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 20 °C
3: H2 S / dimethylformamide / 0.25 h
Reference：
[1]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
[2]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
24
[ 13691-26-4 ]
benzyl-4-[2,2,2-trifluoro-N-(p-nitrophenyl)acetamido]butanedithioate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: CH2 Cl2 / 0.5 h / 20 °C
2: 2,6-di-t-butylpyridine / CH2 Cl2 / 0.5 h
3: H2 S / dimethylformamide / 0.25 h
4: 198 mg / Et3 N / CH2 Cl2 / 2 h / 25 °C
Multi-step reaction with 4 steps
1: 97 percent / Lawesson's reagent / tetrahydrofuran / 24 h / Heating
2: CH2 Cl2 / 20 °C
3: H2 S / dimethylformamide / 0.25 h
4: 198 mg / Et3 N / CH2 Cl2 / 2 h / 25 °C
Reference：
[1]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
[2]Lacroix, Simon; Rixhon, Vinciane; Marchand-Brynaert, Jacqueline
[Synthesis, 2006, # 14, p. 2327 - 2334]
25
[ 13691-26-4 ]
methyl 4-amino-N-(4-nitrophenyl)butanoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: NaOH / H2 O
2: 83 percent / diethyl ether
26
[ 13691-26-4 ]
[ 116614-83-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 96 percent / P2 S5 / benzene / Heating
2: CH2 Cl2 / 78 h / 50 °C
3: Ph3 P, Et3 N / CH2 Cl2 / 2 h / Ambient temperature
27
[ 13691-26-4 ]
5-Methoxycarbonylmethylsulfanyl-1-(4-nitro-phenyl)-3,4-dihydro-2H-pyrrolium; bromide
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 96 percent / P2 S5 / benzene / Heating
2: CH2 Cl2 / 78 h / 50 °C
28
[ 58973-27-6 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: CH2 Cl2 / 78 h / 50 °C
2: Ph3 P, Et3 N / CH2 Cl2 / 2 h / Ambient temperature
29
[ 100-01-6 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 3 h / 200 - 210 °C
2: H2 SO4 / 2 h / Heating
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 6 h / 20 °C
2: aluminum oxide; ammonium iodide / 0.5 h / 200 °C / Microwave irradiation
Reference：
[1]Michael,J.P.; Hosken,G.D.; Howard,A.S.
[Tetrahedron, 1988, vol. 44, p. 3025]
[2]Lebedev, A. T.; Mazur, D. M.; Kudelin, A. I.; Fedotov, A. N.; Gloriozov, I. P.; Ustynyuk, Yu. A.; Artaev, V. B.
[Rapid Communications in Mass Spectrometry, 2016, p. 2416 - 2422]
30
[ 13691-26-4 ]
[ 10466-75-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: mixed acid
2: 2 M aq. NaOH / 0.5 h / Ambient temperature
31
[ 13691-26-4 ]
[ 86147-74-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aqueous Ba(OH)2
2: nickel-chromium oxide; H2 O / 80 °C / 147102 Torr / Hydrogenation
32
[ 13691-22-0 ]
[ 13691-26-4 ]
33
[ 616-45-5 ]
[ 636-98-6 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
80%
With copper (I) iodide; Cs2 CO3 ; cobalt(II) 2,4-pentanedionate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h; Inert atmosphere;
8%
With copper carbonate hydroxide; Cs2 CO3 ; Ethane-1,2-diamine In 2-methyltetrahydrofuran at 110℃; for 24h; Sealed tube;
4.2 General procedure for the preparationof N-arylamides 3
General procedure: The corresponding aryl halide (1, 3.00 mmol) and amide(2, 3.60 mmol) were dissolved in 2-MeTHF (6 mL) in a40-mL vial, then 1,2-ethylenediamine (EDA, 3.00 mmol),Cs2CO3(7.50 mmol) and malachite (50.0 mg, 13.0 mol%)were added to this solution. The vial was then sealed with astopper and the reaction was stirred for 24 h at 110 °C. Themixture was then filtered, then washed with EtOAc (60 mL).After evaporation of the filtrate, the residue was purifiedby flash column chromatography. An analytical sample wasrecrystallized from the solvent given below after the meltingpoint. Compounds 3a-g, 3i-l and 3o-an are known in theliterature, while compounds 3h,m,n are new.
70 %Chromat.
With tripotassium phosphate tribasic; copper (I) iodide In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere; Glovebox;
Reference：
[1]Kundu, Debasish; Tripathy, Manisha; Maity, Pintu; Ranu, Brindaban C.
[Chemistry - A European Journal, 2015, vol. 21, # 24, p. 8727 - 8732]
[2]Bezúr, László; Dancsó, András; Györke, Gábor; Hunyadi, Dávid; Milen, Mátyás; Szalóki, Imre; Volk, Balázs
[Catalysis Letters, 2022]
[3]Gueell, Imma; Ribas, Xavi
[European Journal of Organic Chemistry, 2014, vol. 2014, # 15, p. 3188 - 3195]
34
[ 13691-26-4 ]
[ 443988-47-4 ]
C25 H32 N2 O5 S
[ No CAS ]
Yield Reaction Conditions Operation in experiment
72%
With dirhodium tetraacetate In toluene at 70℃; for 16h;
35
[ 13691-26-4 ]
[ 20098-55-9 ]
C20 H30 N2 O5 S
[ No CAS ]
Yield Reaction Conditions Operation in experiment
68%
With dirhodium tetraacetate In toluene at 70℃; for 16h;
36
[ 13691-26-4 ]
(R)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one
[ No CAS ]
[ 1621326-32-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: trichlorophosphate / dichloromethane / 3 h
1.2: 18 h / 50 °C / Inert atmosphere; Reflux
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere
3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 16 h / -78 - -10 °C / Inert atmosphere
Reference：
[1]Kepiro, Miklos; Varkuti, Boglarka H.; Vegner, Laszlo; Voeroes, Gergely; Hegyi, Gyoergy; Varga, Mate; Malnasi-Csizmadia, Andras
[Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8211 - 8215][Angew. Chem., 2014, vol. 126, # 31, p. 8350 - 8354]
37
[ 13691-26-4 ]
[ 1621326-30-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: trichlorophosphate / dichloromethane / 3 h
1.2: 18 h / 50 °C / Inert atmosphere; Reflux
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 - 0 °C / Inert atmosphere
Reference：
[1]Kepiro, Miklos; Varkuti, Boglarka H.; Vegner, Laszlo; Voeroes, Gergely; Hegyi, Gyoergy; Varga, Mate; Malnasi-Csizmadia, Andras
[Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8211 - 8215][Angew. Chem., 2014, vol. 126, # 31, p. 8350 - 8354]
38
[ 13691-26-4 ]
[ 18595-16-9 ]
methyl 2-[(2E)-1-(4-nitrophenyl)pyrrolidin-2-ylidene]amino}-5-methylbenzoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
10%
Stage #1: 2-amino-5-methylbenzoic acid methyl ester With trichlorophosphate In dichloromethane for 3h;
Stage #2: 1-(4-nitrophenyl)pyrrolidin-2-one In dichloromethane at 50℃; for 18h; Inert atmosphere; Reflux;
Reference：
[1]Kepiro, Miklos; Varkuti, Boglarka H.; Vegner, Laszlo; Voeroes, Gergely; Hegyi, Gyoergy; Varga, Mate; Malnasi-Csizmadia, Andras
[Angewandte Chemie - International Edition, 2014, vol. 53, # 31, p. 8211 - 8215][Angew. Chem., 2014, vol. 126, # 31, p. 8350 - 8354]
39
diphenyl(trifluoromethanesulfonato)-λ3 -iodane
[ No CAS ]
[ 13691-26-4 ]
1-(5-nitrobiphenyl-2-yl)pyrrolidin-2-one
[ No CAS ]
Yield Reaction Conditions Operation in experiment
54%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) triflimide; Trimethylacetic acid In cyclohexane at 100℃; for 12h; Schlenk technique; Molecular sieve; Inert atmosphere; regioselective reaction;
40
[ 616-45-5 ]
[ 586-78-7 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
95%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux; Inert atmosphere;
41
[ 13691-26-4 ]
[ 18595-16-9 ]
C19 H19 N3 O4
[ No CAS ]
Yield Reaction Conditions Operation in experiment
20%
General procedure: The preparation of amidines was adopted from Verhasselt et al.[19].A flame-dried bulb of 250 mL, kept under a nitrogen atmosphere,was loaded with 120 mL of dry dichloromethane and pyrrolidinone(43.9 mmol, 1 equiv). Next, 8.18 mL of POCl3 (87.7 mmol,2 equiv) was added and the resulting mixture was stirred at roomtemperature for 24 h. Afterwards, a solution of <strong>[18595-16-9]methyl 2-amino-5-methylbenzoate</strong> (22) (7.61 g, 46.0 mmol, 1.05 equiv) in drydichloromethane (45 mL) was added via cannula and the reactionmixture was heated to 35 C for 24 h. Then, the reaction mixturewas cooled to 0 C, basified with 3 M aqueous NaOH until the pHequaled 10 and subsequently extracted with ethyl acetate (450 mLand 150 mL). The combined organic layers were washed with300 mL of brine, dried over magnesium sulfate and evaporated invacuo.
42
[ 13691-26-4 ]
(R)-3a-hydroxy-6-methyl-1-(4-nitrophenyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one
[ No CAS ]
[ 1621326-32-6 ]
C38 H36 N6 O8
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: trichlorophosphate / dichloromethane / 24 h / 20 °C / Inert atmosphere
1.2: 96 h / 35 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
2.2: 16 h / -15 °C / Inert atmosphere
43
[ 13691-26-4 ]
(S)-1-(4-aminophenyl)-3a-hydroxy-6-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]quinolin-4-one
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: trichlorophosphate / dichloromethane / 24 h / 20 °C / Inert atmosphere
1.2: 96 h / 35 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
2.2: 16 h / -15 °C / Inert atmosphere
3.1: palladium 10% on activated carbon; ammonium formate / methanol / 0.25 h / 20 °C
44
[ 13691-26-4 ]
[ 2393-23-9 ]
[ 10220-22-1 ]
N<SUP>1</SUP>-(4-methoxybenzyl)-N<SUP>4</SUP>-(4-nitrophenyl)butane-1,4-diamine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 39%
2: 40 %Chromat.
Stage #1: 1-(4-nitrophenyl)pyrrolidin-2-one With Schwartz's reagent In tetrahydrofuran at 0℃; for 1h; Sealed tube; Inert atmosphere;
Stage #2: 4-methoxy-benzylamine With sodium tris(acetoxy)borohydride In tetrahydrofuran at 23℃; for 18h; Sealed tube; Inert atmosphere;
Reference：
[1]Prince, Robin J.; Gao, Fang; Pazienza, Jessica E.; Marx, Isaac E.; Schulz, Jurgen; Hopkins, Brian T.
[Journal of Organic Chemistry, 2019, vol. 84, # 12, p. 7936 - 7949]
45
[ 616-45-5 ]
[ 100-00-5 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
88%
With palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene; acetonitrile at 140℃; for 1.11667h; Flow reactor;
46
[ 10220-22-1 ]
[ 124-38-9 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
98%
With sodium chlorate In lithium hydroxide monohydrate; acetonitrile at 60℃; for 1.5h; Green chemistry;
General procedure for the oxidation of tertiary amines to corresponding amides:
General procedure: A solution of (4-nitrophenyl) morpholine (1.04 g, 5 mmol) in CH3CN (10mL) was added into a 100mL three-port roundbottomflask, and it was stirred under CO2 atmosphere at 50°C. Then a solution of sodium chlorite (morethan 80%, 1.69 g, 15mmol) in 5 mL water was added in 20 min. TLC and HPLC showed that the reactionwas completed in 2.5 h. The reaction was quenched with aqueous saturated sodium sulfite. The mixture wasextracted by DCM (3×30 mL). The combined organic solution was dried over anhydrous sodium sulphate.Removal of all volatiles heft a residue, which was purified by flash chromatography on silica gel(hexane/EtOAc, from 5:1 to 3:1) to give 1.05g (95% yield) of 2a as a light-yellow solid.
Reference：
[1]Liu, Chaoyang; Sun, Haozhou; Qin, Cheng; Yang, Tiannuo; Zhang, Wenxian; Zhou, Yuan; Li, Yani; Jia, Zheng Robert; Chu, Changhu
[Synlett, 2022, vol. 33, # 10, p. 993 - 997]
47
[ 350-46-9 ]
[ 13691-26-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium carbonate / dimethyl sulfoxide / 2 h / 100 °C / Green chemistry
2: sodium chlorate / acetonitrile; lithium hydroxide monohydrate / 1.5 h / 60 °C / 760.05 Torr / Green chemistry
Reference：
[1]Liu, Chaoyang; Sun, Haozhou; Qin, Cheng; Yang, Tiannuo; Zhang, Wenxian; Zhou, Yuan; Li, Yani; Jia, Zheng Robert; Chu, Changhu
[Synlett, 2022, vol. 33, # 10, p. 993 - 997]
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