Alternatived Products of [ 23239-88-5 ]
Product Details of [ 23239-88-5 ]
CAS No. : 23239-88-5
MDL No. : MFCD00012999
Formula :
C9 H12 ClNO2
Boiling Point :
-
Linear Structure Formula : -
InChI Key : JAADDQHUJDUAKW-UHFFFAOYSA-N
M.W :
201.65
Pubchem ID : 10214462
Synonyms :
Benzocaine hydrochloride;Ethyl 4-aminobenzoate hydrochloride;Ethyl p-aminobenzoate hydrochloride
Chemical Name : Ethyl 4-aminobenzoate hydrochloride
Calculated chemistry of [ 23239-88-5 ]
Physicochemical Properties
Num. heavy atoms :
13
Num. arom. heavy atoms :
6
Fraction Csp3 :
0.22
Num. rotatable bonds :
3
Num. H-bond acceptors :
2.0
Num. H-bond donors :
1.0
Molar Refractivity :
53.9
TPSA :
52.32 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
Yes
P-gp substrate :
No
CYP1A2 inhibitor :
No
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
No
CYP2D6 inhibitor :
No
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-5.64 cm/s
Lipophilicity
Log Po/w (iLOGP) :
0.0
Log Po/w (XLOGP3) :
2.66
Log Po/w (WLOGP) :
2.26
Log Po/w (MLOGP) :
1.94
Log Po/w (SILICOS-IT) :
1.31
Consensus Log Po/w :
1.63
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-2.91
Solubility :
0.248 mg/ml ; 0.00123 mol/l
Class :
Soluble
Log S (Ali) :
-3.41
Solubility :
0.0784 mg/ml ; 0.000389 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-2.51
Solubility :
0.622 mg/ml ; 0.00308 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
1.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.31
Safety of [ 23239-88-5 ]
Signal Word: Warning
Class: N/A
Precautionary Statements: P261-P280
UN#: N/A
Hazard Statements: H317
Packing Group: N/A
GHS Pictogram:
Application In Synthesis of [ 23239-88-5 ]
* 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.
Upstream synthesis route of [ 23239-88-5 ]
Downstream synthetic route of [ 23239-88-5 ]
1
[ 75-44-5 ]
[ 23239-88-5 ]
[ 30806-83-8 ]
Yield Reaction Conditions Operation in experiment
With 1,2-dichloro-benzene at 170℃;
With 1,2-dichloro-benzene at 170℃;
2
[ 14189-83-4 ]
[ 23239-88-5 ]
[ 116132-26-4 ]
Yield Reaction Conditions Operation in experiment
With ethanol
With acetic acid
Reference:
[1]Grigor'ewa et al.
[Zhurnal Obshchei Khimii, 1959, vol. 29, p. 935,937, 938; engl. Ausg. S. 916, 918, 920]
[2]Grigor'ewa et al.
[Zhurnal Obshchei Khimii, 1959, vol. 29, p. 935,937, 938; engl. Ausg. S. 916, 918, 920]
3
[ 2461-83-8 ]
[ 23239-88-5 ]
[ 102892-96-6 ]
Yield Reaction Conditions Operation in experiment
With ethanol at 120℃;
4
[ 23239-88-5 ]
[ CAS Unavailable ]
[ 5429-14-1 ]
Yield Reaction Conditions Operation in experiment
With water
5
[ 23239-88-5 ]
[ 51934-41-9 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; sodium nitrite Diazotization. Erwaermen der erhaltenen Diazoniumsalz-Loesung mit wss. Kaliumjodid-Loesung;
6
[ 23239-88-5 ]
[ 117920-44-2 ]
Yield Reaction Conditions Operation in experiment
With trichlorophosphate
7
[ 23239-88-5 ]
[ 110-13-4 ]
[ 5159-70-6 ]
Yield Reaction Conditions Operation in experiment
With ethanol
8
[ 23239-88-5 ]
[ 461-58-5 ]
[ 406498-85-9 ]
Yield Reaction Conditions Operation in experiment
With pyridine
With ethanol
Reference:
[1]Shapiro et al.
[Journal of the American Chemical Society, 1957, vol. 79, p. 5064,5069][Journal of the American Chemical Society, 1959, vol. 81, p. 3728,3729]
[2]Cattapan; Vercellone
[Gazzetta Chimica Italiana, 1955, vol. 85, p. 345,347]
9
[ 23239-88-5 ]
[ 495-71-6 ]
[ 102882-92-8 ]
Yield Reaction Conditions Operation in experiment
With ethanol at 100℃;
10
[ 2185-00-4 ]
[ 23239-88-5 ]
[ 38219-44-2 ]
Yield Reaction Conditions Operation in experiment
In N,N-dimethyl-formamide Ambient temperature;
11
[ 23239-88-5 ]
[ 583-47-1 ]
[ 23961-20-8 ]
12
[ 23239-88-5 ]
[ 2224-52-4 ]
[ 52238-26-3 ]
13
[ 497-25-6 ]
[ 23239-88-5 ]
[ 86234-55-1 ]
Yield Reaction Conditions Operation in experiment
61%
In various solvent(s) at 160 - 170℃;
14
[ 99-77-4 ]
[ 23239-88-5 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; hydrogen In ethanol for 0.5h;
15
[ 23239-88-5 ]
[ 83325-25-1 ]
[ 83325-17-1 ]
Yield Reaction Conditions Operation in experiment
29%
With N,N-dimethyl-cyclohexanamine; phosphorus pentoxide at 150℃; for 0.75h;
16
[ 23239-88-5 ]
[ 122473-44-3 ]
Yield Reaction Conditions Operation in experiment
With ethanol
17
[ 23239-88-5 ]
[ 163814-12-8 ]
[ 328236-52-8 ]
Yield Reaction Conditions Operation in experiment
74%
With sodium cyanoborohydride In methanol at 20℃; for 16h;
Reference:
[1]Raoul, Marion; Schaeffer, Corinne; Leonce, Stephane; Pierre, Alain; Atassi, Ghanem; Hocquemiller, Reynald; Lewin, Guy
[Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 1, p. 79 - 81]
18
[ 1762-95-4 ]
[ 23239-88-5 ]
[ 23051-16-3 ]
Yield Reaction Conditions Operation in experiment
38%
With sodium hydrogensulfite In water at 80 - 90℃; for 1.5h;
19
[ 64-17-5 ]
[ 150-13-0 ]
[ 23239-88-5 ]
Yield Reaction Conditions Operation in experiment
85%
With thionyl chloride for 6h; Heating;
With thionyl chloride for 2h; Heating;
Reference:
[1]Zafar, Abdullah; Melendez, Rosa; Geib, Steven J; Hamilton, Andrew D
[Tetrahedron, 2002, vol. 58, # 4, p. 683 - 690]
[2]Lebedev; Lebedeva; Sheludyakov; Ovcharuk; Kovaleva; Ustinova
[Russian Journal of General Chemistry, 2006, vol. 76, # 7, p. 1069 - 1080]
20
[ 23239-88-5 ]
[ 105958-84-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: 38 percent / NaHSO3 / H2 O / 1.5 h / 80 - 90 °C
2: methanol / 1 h / Heating
3: 0.6 g / dimethylsulfoxide / 15 h / 70 - 110 °C
4: 68 percent / LiOH*H2 O / ethanol; H2 O / 4 h / Heating
21
[ 23239-88-5 ]
[ 210963-81-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 38 percent / NaHSO3 / H2 O / 1.5 h / 80 - 90 °C
2: methanol / 1 h / Heating
3: 0.6 g / dimethylsulfoxide / 15 h / 70 - 110 °C
22
[ 23239-88-5 ]
[ 417725-71-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 38 percent / NaHSO3 / H2 O / 1.5 h / 80 - 90 °C
2: methanol / 1 h / Heating
23
[ 23239-88-5 ]
[ 57362-77-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: aqueous hydrochloric acid; sodium nitrite / Diazotization. Erwaermen der erhaltenen Diazoniumsalz-Loesung mit wss. Kaliumjodid-Loesung
2: sulfuric acid; aqueous nitric acid
24
[ 23239-88-5 ]
[ 6285-96-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: aqueous hydrochloric acid; sodium nitrite / Diazotization. Erwaermen der erhaltenen Diazoniumsalz-Loesung mit wss. Kaliumjodid-Loesung
2: sulfuric acid; aqueous nitric acid
3: copper-powder; nitrobenzene
25
[ 23239-88-5 ]
[ 855200-39-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: water
2: aqueous ammonia
3: ethanol; iodine
26
[ 23239-88-5 ]
[ 99254-22-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: water
2: aqueous ammonia
27
[ 7149-03-3 ]
[ 865139-46-4 ]
[ 23239-88-5 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; In ethyl acetate;
To a solution of ethyl 4-aminobenzoate (10.0 g, 59.3 mmol) and triethylamine (18.4 mL, 130 mmol) in acetic acid (30 mL) was slowly added dropwise bromine (3.04 mL, 59.3 mmol) under stirring at room temperature. The reaction mixture was stirred at room temperature for 2 hr and cold water (400 mL) was added. The precipitated solid was collected by filtration, washed with cold water and vacuum dried to give crude ethyl 4-amino-3-bromobenzoate (15.0 g) as red-pink crystals.
28
[ 497-25-6 ]
[ 111-77-3 ]
[ 23239-88-5 ]
[ 86234-55-1 ]
Yield Reaction Conditions Operation in experiment
61%
6 Preparation of Ethyl 4[N-(2-aminoethyl)]aminobenzoate
EXAMPLE 6 Preparation of Ethyl 4[N-(2-aminoethyl)]aminobenzoate In a manner similar to the above two examples, ethyl p-aminobenzoate hydrochloride (21.7 g, 0.11 mole), 2-oxazolidinone (8.8 g, 0.10 mole) and 50 ml of 2-(2-methoxyethoxy)ethanol was heated to 175° C. for two hours. Removal of solvent and workup gave 23.1 g of the crude product as a dark yellow liquid. Kugelrohr distillation (bulb to bulb) at 130° C. to 160° C. (oven temperature) (0.1 mm Hg) afforded a 61 percent yield of the diamine as a clear liquid which slowly solidified on standing at ambient temperatures to a white waxy solid. Spectral evidence confirmed its structure.
29
[ CAS Unavailable ]
[ 23239-88-5 ]
[ 67-63-0 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
In water
1 Preparation of N,N"-bis(4-ethoxycarbonylphenyl)-3,12-diimino-2,4,11,13-tetraazatetradecanediimidamide dihydrochloride:
STR4 A mixture of 4.0 g (20 moles) ethyl p-aminobenzoate hydrochloride, 2.25g (9 moles) 1,6-hexanebis(3'-cyanoguanidine), and 15 ml 2-propanol was brought quickly to boiling and stirred under reflux for 10 minutes. The reaction mixture which set to a solid mass was transferred to a funnel and washed with hot 2-propanol. The washed product was dried on a steam bath and 4.1g (70% of theoretical yield) of a white powder was recovered. After recrystallizing from water, a microcrystalline powder having a melting point of 235°-7° C was recovered. Analysis for C28 H40 N10 O4 2HCl:
30
[ CAS Unavailable ]
[ 23239-88-5 ]
[ CAS Unavailable ]
Yield Reaction Conditions Operation in experiment
52%
With DCC In acetonitrile mixt. of Mo compd. (1 mmol), DCC (3 mmol), and ligand (2 mmol) refluxed in dry MeCN for 12 h; cooled to room temp., filtered, concd., crystd., fltered off, washed (EtOH, Et2O), recrystd. (acetone/EtOH=1/1), elem. anal.;
31
[ 23239-88-5 ]
[ 79-09-4 ]
[ 132371-06-3 ]
Yield Reaction Conditions Operation in experiment
94%
Stage #1: propionic acid With iodine; triethylamine; phosphorous acid trimethyl ester In dichloromethane for 0.166667h; Cooling with ice; Inert atmosphere;
Stage #2: benzocaine hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice;
32
[ 23239-88-5 ]
[ 1398090-37-3 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: acetic acid / 1,2-dichloro-ethane / 80 - 85 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 24 h / 26 °C / Inert atmosphere
Reference:
[1]Shah, Kiran; Patel, Dipam; Jadav, Pradip; Sheikh, Mubeen; Sairam, Kalapatapu V. V. M.; Joharapurkar, Amit; Jain, Mukul R.; Bahekar, Rajesh
[Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 18, p. 5857 - 5862,6]
33
[ 23239-88-5 ]
[ 1398089-40-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: acetic acid / 1,2-dichloro-ethane / 80 - 85 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 24 h / 26 °C / Inert atmosphere
3: diisopropylamine / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
4: water; lithium hydroxide / tetrahydrofuran / 24 h / 26 °C / Inert atmosphere
Reference:
[1]Shah, Kiran; Patel, Dipam; Jadav, Pradip; Sheikh, Mubeen; Sairam, Kalapatapu V. V. M.; Joharapurkar, Amit; Jain, Mukul R.; Bahekar, Rajesh
[Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 18, p. 5857 - 5862,6]
34
[ 23239-88-5 ]
[ 1398089-86-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: acetic acid / 1,2-dichloro-ethane / 80 - 85 °C / Inert atmosphere
2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 24 h / 26 °C / Inert atmosphere
3: diisopropylamine / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere
Reference:
[1]Shah, Kiran; Patel, Dipam; Jadav, Pradip; Sheikh, Mubeen; Sairam, Kalapatapu V. V. M.; Joharapurkar, Amit; Jain, Mukul R.; Bahekar, Rajesh
[Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 18, p. 5857 - 5862,6]
35
[ 67-36-7 ]
[ 23239-88-5 ]
[ 3782-83-0 ]
Yield Reaction Conditions Operation in experiment
With acetic acid In 1,2-dichloro-ethane at 80 - 85℃; Inert atmosphere;
General Procedure for synthesis of compounds 6
General procedure: A compound 4 (1.0 eq.) and aniline 5 (1.0 eq.) in dichloroethane were treated with glacial acetic acid (4.0 eq.) at 80°C for 4 h, The reaction mixture was cooled to room temperature, treated with sodium triacetoxyborohydride (2.0 eq.) and stirred overnight at room temperature. The mixture was poured into saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and the filtrate was concentrated under reduced pressure. The residue was purified by column Chromatography (100-200 mesh size silica gel, 0-20% ethyl acetate: hexane) afforded the title compound 6.
Reference:
[1]Shah, Kiran; Patel, Dipam; Jadav, Pradip; Sheikh, Mubeen; Sairam, Kalapatapu V. V. M.; Joharapurkar, Amit; Jain, Mukul R.; Bahekar, Rajesh
[Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 18, p. 5857 - 5862,6]
36
[ 2936-08-5 ]
[ 23239-88-5 ]
[ 690988-44-4 ]
Yield Reaction Conditions Operation in experiment
82%
With triethylamine In dichloromethane at 0 - 20℃;
Synthesis of Ethyl 4-(2-Propylpentanamido)benzoate (VABE, 14)
Ethyl 4-aminobenzoate 13 (25 mmol) was mixed with triethylamine (25 mmol) in 200 mL dichloromethane. While a continuous stirring at 0°C; freshly distilled valproyl chloride (25 mmol) mixed with 50 mL dichloromethane was added dropwise and the reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (50 mL), the organic phase washed with water, and dried over MgSO4 anhydrous. Filtered and the solvent was removed with a rotary evaporator to afford 14 in yield 6 g (82%) as an oily product.
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
37
[ 23239-88-5 ]
[ 1610368-79-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
38
[ 23239-88-5 ]
[ 1638254-75-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
39
[ 23239-88-5 ]
[ 1638254-76-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
40
[ 23239-88-5 ]
[ 1638254-77-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
41
[ 23239-88-5 ]
[ 1638254-78-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
42
[ 23239-88-5 ]
[ 1638254-79-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
43
[ 23239-88-5 ]
[ 1638254-80-4 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
44
[ 23239-88-5 ]
[ 1638254-81-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
45
[ 23239-88-5 ]
[ 1638254-82-6 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
46
[ 23239-88-5 ]
[ 1638254-83-7 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 0 - 20 °C
2: hydrazine / methanol / 4 h / Reflux
3: acetic acid / methanol / 8 h / Reflux
Reference:
[1]El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine Nabil; Elkayal, Ahmed Mohamed; Ibrahim, Mahmoud Fawzy; Abutaha, Nael; Wadaan, Mohammad Ahmad; Hamed, Ezzat Awad
[Chemical and Pharmaceutical Bulletin, 2014, vol. 62, # 6, p. 591 - 599]
47
[ 574-17-4 ]
[ 23239-88-5 ]
ethyl 4-(2-(2-acetamidophenyl)-2-oxoacetamido)benzoate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
87%
With potassium carbonate In acetonitrile at 20℃;
General Method for the synthesis of 4a-f
General procedure: L-Amino acid ester (12 mmol) and K2CO3 (1.66 g, 12 mmol) were added to the solution of N-acetylisatin 1 (1.89 g, 10 mmol) in CH3CN (50 mL) with intensive stirring. This mixture was stirred at room temperature overnight. The reaction mixture was then filtered and washed with 10 mL of acetonitrile. The solvent was removed under vacuum to dryness, and the crude product was recrystallized from dichloromethane-hexane to afford the pure product.
Reference:
[1]El-Faham, Ayman; Al Marhoon, Zainab; Abdel-Megeed, Ahmed; Khattab, Sherine N.; Bekhit, Adnan A.; Albericio, Fernando
[Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 1, p. 70 - 74]
48
[ 23239-88-5 ]
[ CAS Unavailable ]
[ 314046-31-6 ]
Yield Reaction Conditions Operation in experiment
81%
In diethyl ether; ethanol at 20℃;
Synthesis of compounds 3, 5, and 7 (general procedure).
General procedure: A 1 : 2 mixture of 5-chloro-4-nitrobenzofurazane in an alcohol-ether binary solvent was stirred at room temperature from 2 h to 2 weeks and then left to stand at room temperature for 2 weeks. Transparent crystals formed and were separated, washed with diethyl ether, and dried. The yields of the reaction products, spectral characteristics, and elemental analyses are listed in Table 1.
Reference:
[1]Galkina; Takhautdinova; Ivshin; Khayarov, Kh. R.; Islamov; Bakhtiyarova, Yu. V.; Yamalieva; Kataeva; Galkin
[Russian Journal of General Chemistry, 2018, vol. 88, # 5, p. 898 - 902][Zh. Obshch. Khim., 2018, vol. 88, # 5, p. 754 - 758,5]
49
[ 94-09-7 ]
[ 865139-46-4 ]
[ 23239-88-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: bromine; acetic acid; triethylamine / 2 h / 20 °C
2: hydrogenchloride / ethyl acetate
50
[ 1121-60-4 ]
[ 50-00-0 ]
[ 23239-88-5 ]
[ 2292262-65-6 ]
Yield Reaction Conditions Operation in experiment
72%
In ethanol; water at 20℃; for 48h; Schlenk technique;
51
[ 94-09-7 ]
[ 23239-88-5 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride In ethanol; water Cooling with ice;
52
[ 23239-88-5 ]
[ 60100-09-6 ]
[ 5422-63-9 ]
Yield Reaction Conditions Operation in experiment
72%
In toluene at 120℃; for 3h; Green chemistry;
53
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 23239-88-5 ]
[ 2902579-73-9 ]
Yield Reaction Conditions Operation in experiment
63 %
With [Rh(acac)(CO)2]; hydrogen; Xantphos In water at 70℃; Microwave irradiation; regioselective reaction;
Reference:
[1]Migliorini, Francesca; Monciatti, Elisabetta; Romagnoli, Giulia; Parisi, Maria Laura; Taubert, Julia; Vogt, Matthias; Langer, Robert; Petricci, Elena
[ACS Catalysis, 2023, vol. 13, # 4, p. 2702 - 2714]