[ CAS No. 19013-15-1 ] {[proInfo.proName]}

Name: 19013-15-1|Ethyl 4-methyl-3-nitrobenzoate|95+%
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3d Animation Molecule Structure of 19013-15-1

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COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 19013-15-1 ]

CAS No. :	19013-15-1	MDL No. :	MFCD06204349
Formula :	C₁₀H₁₁NO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FWOACYVHDUBZDT-UHFFFAOYSA-N
M.W :	209.20	Pubchem ID :	14945864
Synonyms :

Calculated chemistry of [ 19013-15-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	56.32
TPSA :	72.12 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.17
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	2.08
Log Po/w (MLOGP) :	1.46
Log Po/w (SILICOS-IT) :	0.39
Consensus Log Po/w :	1.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.83
Solubility :	0.308 mg/ml ; 0.00147 mol/l
Class :	Soluble
Log S (Ali) :	-3.81
Solubility :	0.0328 mg/ml ; 0.000157 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.65
Solubility :	0.465 mg/ml ; 0.00222 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.12

Safety of [ 19013-15-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 19013-15-1 ]

* 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 [ 19013-15-1 ]
Downstream synthetic route of [ 19013-15-1 ]

[ 19013-15-1 ] Synthesis Path-Upstream 1~2

1
[ 19013-15-1 ]
[ 107516-75-6 ]

Reference： [1] Patent: WO2011/71716, 2011, A1,
[2] Patent: WO2014/149164, 2014, A1,

2
[ 19013-15-1 ]
[ 41191-92-8 ]

Reference： [1] Journal of the American Chemical Society, 1993, vol. 115, # 8, p. 3199 - 3211
[2] European Journal of Organic Chemistry, 2010, # 24, p. 4662 - 4670

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Isomers

Technical Information

• Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amines Convert Esters into Amides • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conversion of Amino with Nitro • Convert Esters into Aldehydes Using a Milder Reducing Agent • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Ester Cleavage • Ester Hydrolysis • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Grignard Reagents Transform Esters into Alcohols • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Hantzsch Pyridine Synthesis • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • Transesterification • Vilsmeier-Haack Reaction

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[ 19013-15-1 ]

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Yield	Reaction Conditions	Operation in experiment
98%	With hydrogenchloride; at 90℃; for 20.0833h;	Example 1 Synthesis of 4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide (1a) and 4-[(4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carbonyl)-amino]-benzoic acid methyl ester (1b) 4-Methyl-3-nitro-benzoic acid (71 g, 0.39 mol) was dissolved in dry EtOH (600 mL) and dry HCl gas was bubbled into the solution for 5 min. The reaction was heated to 90 C. under N2 for 20 h, then cooled and concentrated to give <strong>[96-98-0]4-methyl-3-nitro-benzoic acid</strong> ethyl ester as a straw-color liquid (80.0 g, yield 98%).
98%	With hydrogenchloride; at 90℃; for 20h;Inert atmosphere;	Intermediate A: Diethyl 1H-indole-2,6-dicarboxylate: Step 1: Synthesis of ethyl 4-methyl-3-nitrobenzoate 4-Methyl-3-nitrobenzoic acid (71 g, 0.39 mol) is dissolved in dry ethanol (600 mL) and dry HCl gas is bubbled into the solution for 5 min. The reaction mixture is heated to 90 C under N2 for 20 h. The solvent is removed under vacuum to afford the title compound as a straw-colored liquid (80.0 g, 98%).
91%	With hydrogenchloride; at -5 - 80℃; for 16h;	Ethyl 4-methyl-3-nitrobenzoate (1): A stirring solution of <strong>[96-98-0]4-methyl-3-nitrobenzoic acid</strong> (10 g, 55.2 mmol) in EtOH (120 mL) at -5 C was bubbled dry HCI gas for 10 minutes and then refluxed at 80 C for 16 h. The reaction mixture was distilled off to obtain crude compound. Crude was dissolved in EtOAc (200 mL) and washed with cold saturated NaHC03 (2x200 mL), water (200 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1 (10.5 g, 91%) as colorless liquid. 1H NMR (500 MHz, DMSO-de) delta 1.33 (t, J = 7.0 Hz, 3H), 2.58 (s, 3H), 4.34 (q, J = 7.0 Hz, 2H), 7.66 (d, J = 7.5 Hz, 1H), 8.43 (d, J = 7.5 Hz, 1H), 8.42 (s, 1H).

Yield	Reaction Conditions	Operation in experiment
60%	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 15h; Heating;
	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 24h; Heating;
	With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 8h; Reflux; Under light;

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: ethyl 4-methyl-3-nitro-benzoate With sodium ethanolate In ethanol; dimethyl sulfoxide Stage #2: 4-(4'-chlorophenoxy)benzaldehyde In ethanol; dimethyl sulfoxide
60%	With ethanol; sodium ethanolate In dimethyl sulfoxide	III.B; 9.a Indole 16 was prepared by generating an anion of 4-methyl-3-nitroethyl benzoate with sodium ethoxide and then condensing the corresponding 4-chloro-phenoxy benzaldehyde thereby giving compound 14 in good yield. Reduction of the nitro group with iron followed by ruthenium catalyzed cyclization led to the indole intermediate 15. Tsuji et al., Org. Chem. 55:580 (1990). Finally, hydrolysis of the ester group gave the target compound 16. Scheme 9.

Yield	Reaction Conditions	Operation in experiment
91%	With sodium ethanolate In ethanol at 0 - 20℃;
77%	With sodium ethanolate In ethanol at 20℃;
77%	With sodium ethanolate In ethanol at 20℃; for 16h;	1 Synthesis of 4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carboxylic acid pyridin-3-ylamide (1a) and 4-[(4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrazino[1,2-a]indole-7-carbonyl)-amino]-benzoic acid methyl ester (1b) To a solution of 4-methyl-3-nitro-benzoic acid ethyl ester (80 g, 0.38 mol) and diethyl oxalate (57.13 mL, 0.42 mol) in EtOH (1 L) was added NaOEt (21 wt % in EtOH, 430 mL, 1.15 mol). The resulting brown solution was stirred at room temperature for 16 h. The reaction was quenched with 3 N HCl and diluted with water (2 L) with cooling and stirring. The resulting white precipitate was filtered off and dried in vacuo to provide 91.1 g of 4-(2-ethoxycarbonyl-2-oxo-ethyl)-3-nitro-benzoic acid ethyl ester, yield 77%.

[ CAS No. 19013-15-1 ] {[proInfo.proName]}

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