120-35-4|3-Amino-4-methoxybenzanilide| Ambeed

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Quality Control of [ 120-35-4 ] Purity: 98% SDS Specification

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Product Details of [ 120-35-4 ]

CAS No. :	120-35-4
Formula :	C₁₄H₁₄N₂O₂
M.W :	242.27
SMILES Code :	O=C(NC1=CC=CC=C1)C2=CC=C(OC)C(N)=C2
MDL No. :	MFCD00017166
InChI Key :	LHMQDVIHBXWNII-UHFFFAOYSA-N
Pubchem ID :	8426

Safety of [ 120-35-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 120-35-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	12
Fraction Csp3	0.07
Num. rotatable bonds	4
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	71.55
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	64.35 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.07
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.35
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	2.08
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.89
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.09

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.86
Solubility	0.332 mg/ml ; 0.00137 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.03
Solubility	0.226 mg/ml ; 0.000934 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.69
Solubility	0.00495 mg/ml ; 0.0000204 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	Yes
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.32 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.58

Application In Synthesis of [ 120-35-4 ]

* 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 [ 120-35-4 ]

[ 120-35-4 ] Synthesis Path-Downstream 1~35

1
[ 120-35-4 ]
[ 94-05-3 ]
<(2-Methoxy-5-phenylcarbamoyl-anilino)-methylen>-cyanessigsaeureethylester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 68 - 72.

2
[ 120-35-4 ]
[ 603-33-8 ]
[ 228422-87-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;copper diacetate; In dichloromethane;	Example 28 4-Methoxy-3-phenylamino-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.2 mmol), triphenylbismuth (2.9 g, 6.6 mmol), copper(II) acetate (1.13 g, 6.2 mmol), and triethylamine (0.62 g, 6.2 mmol) to give a solid which was recrystallized from ethanol then subjected to chromatography on a column of silica gel in dichloromethane to afford the product (0.8 g); m.p. 194-195 C. after an additional recrystallization from ethyl alcohol. Calculated for C20H18N2O2: C, 75.45; H, 5.70; N, 8.80. Found: C, 74.66; H, 5.43; N, 8.67.

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 7747 - 7749.
[2]Patent: US6268387,2001,B1 .

3
[ 120-35-4 ]
[ 83724-41-8 ]
3-(2-methoxy-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;copper diacetate;	Example 29 3-(2-Methoxy-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (0.8 g, 3.2 mmol), tris(2-methoxyphenyl)bismuthine (1.8 g, 3.4 mmol), copper(II) acetate (0.6 g, 3.4 mmol), and triethylamine (0.34 g, 3.4 mmol) to afford the product (0.9 g); m.p. 155-156 C. after chromatography on a column of silica gel in chloroform followed by recrystallization from ethanol.

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 7747 - 7749.
[2]Patent: US6268387,2001,B1 .

4
[ 120-35-4 ]
[ 33756-91-1 ]
3-(3-chlorophenylamino)-4-methoxy-N-phenylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;copper diacetate; In chloroform; ethyl acetate;	Example 31 3-(3-Chloro-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.2 mmol), tris(3-chlorophenyl)bismuthine (3.5 g, 6.4 mmol), copper(II) acetate (1.16 g, 6.4 mmol), and triethylamine (0.65 g, 6.4 mmol) to give a solid which was purified by chromatography on a column of silica gel in chloroform/ethyl acetate 99:1 to afford the product (1.8 g); m.p. 168-170 C. after recrystallization from ethanol. Calculated for C20H17ClN2O2: C, 68.09; H, 4.86; N, 7.94. Found: C, 67.91; H, 4.71; N, 7.80.

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 7747 - 7749.
[2]Patent: US6268387,2001,B1 .

5
[ 120-35-4 ]
tris(3,5-dimethylphenyl)-bismuthine [ No CAS ]
3-(3,5-dimethyl-phenylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;copper diacetate;	Example 36 3-(3,5-Dimethyl-phenylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 25 using 3-amino-4-methoxy-N-phenyl-benzamide (1.5 g, 6.3 mmol), tris(3,5-dimethylphenyl)-bismuthine (3.3 g, 6.3 mmol), copper(II) acetate (1.15 g, 6.3 mmol), and triethylamine (0.64 g, 6.3 mmol) to afford the product (1.1 g); m.p. 198-199 C. after recrystallization from a mixture of dichloromethane and ethyl acetate 10:1. Calculated for C22H22N2O2.0.5CH2Cl2: C, 75.52; H, 6.35; N, 7.99. Found: C, 75.56; H, 6.32; N, 7.92.

References: [1]Journal of Organic Chemistry,2000,vol. 65,p. 7747 - 7749.
[2]Patent: US6268387,2001,B1 .

6
[ 120-35-4 ]
C₁₄H₁₂N₃O₂⁽¹⁺⁾*Na⁽¹⁺⁾ [ No CAS ]

References: [1]Patent: WO2005/105928,2005,A1 .Location in patent: Page/Page column 15.

7
[ 120-35-4 ]
[ 55805-64-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In water; at 0℃; for 1h;	(EXAMPLE 7); (Preparation of Solution A); In 75 g of ultra pure water is dispersed 5 g (0.021 mol) of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong>, and the resultant dispersion is cooled to 0C with stirring in an ice bath to which methanol has been added. Further, 6 g (0.058 mol) of 35% hydrochloric acid is added, and the resultant mixture is stirred for 10 minutes. Thereafter, 1.45 g (0.021 mol) of sodium nitrite is dissolved in 2 ml of ultra pure water, and the solution is then added to the mixture. After stirring the mixture for 60 minutes, 0.2 g (0.002 mol) of sulfamic acid is added to eliminate nitrous acid, thereby preparing a diazonium salt solution.
	With hydrogenchloride; sodium nitrite; at 5℃;Industry scale;Product distribution / selectivity;	3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.025 mole/L diazo solution of pH 4.0 (40 L, solution temperature: 5 C.). On the side, N-(4-chloro-2,5-dimethoxyphenyl)-3-hydroxy-2-napthaleneca rboxamide (naphthol AS-LC) (362 parts) was dissolved in an aqueous solution, which contained sodium hydroxide (100 parts), to prepare a 0.126 mole/L grounding solution (8 L, solution temperature: 20 C.); 3-Amino-4-methoxybenzanilide was diazotized in a manner known per se in the art by using a 3.5-fold molar amount of hydrochloric acid and an equimolar amount of sodium nitrite, followed by the addition of sodium acetate to prepare a 0.05 mole/L diazo solution of pH 4.0 (20 L, solution temperature: 5 C.). As a grounding solution, on the other hand, the grounding solution (8L, solution temperature: 20 C.) prepared in Example 3 was used. As illustrated in FIG. 3, the diazo solution was next caused to flow as a first fluid I at a flow rate of 5 L/min by the feed pump d from the first feed tank 2 into the ejector 1 through the first flow path a. Owing to depressurization occurred in the ejector 1, the grounding solution was drawn as a second fluid II at a flow rate of 1 L/min (adjusted by the first flow control means e) from the second feed tank 3 through the second flow path b into the ejector 1 maintained at 20 C. by the temperature control means g, and through a coupling reaction, a naphthol AS pigment (PR146) was yielded.
		Open the exhaust butterfly valve,2000KG water was injected into the diazo reaction tank,29.3 parts of hydrochloric acid was added and the agitator was started.14.6 parts of red-based KD were added from the manhole,Stirred for 10 minutes,Cooled to 0 C or lower with ice,A solution of 4.6 parts of sodium nitrite, which was completely dissolved, was quickly added,A minute later with potassium iodide test paper was purple.Maintaining the temperature of the diazo component below 5 C,After 1.5 hours, 0.5 parts of sulfamic acid (preliminarily dissolved) was added,Two minutes after potassium iodide test strip diazonium salt solution is colorless,Turn off the blender butterfly valve.

References: [1]Patent: WO2006/59741,2006,A1 .Location in patent: Page/Page column 21.
[2]Patent: US2006/86290,2006,A1 .Location in patent: Page/Page column 7; 10.
[3]Patent: CN106317946,2017,A .Location in patent: Paragraph 0018; 0029; 0030.

Yield	Reaction Conditions	Operation in experiment
		Exemplary amines and diamines useful in the invention are: ... 2-methoxy-5-nitro-aniline 5-aminoisophthalic acid dimethyl ester 2-aminobenzoic acid 2-trifluoromethylaniline 3-amino-4-methoxybenzanilide
		2,4- and 2,5-dichloraniline, ... 2-methoxy-5-methyl-4-aminobenzene sulphonic acid methyl amide, 2,5-dimethoxy-4-aminobenzoic sulphonic acid anilide, 2-methoxy-5-methyl-4-benzoylaminoaniline, 4-ethoxy-3-aminobenzamide, 4-methoxy-3-aminobenzoic acid anilide, 4-methyl-3-aminobenzoic acid -2'4'-dimethylanilide, 4-methyl-3-aminobenzoic acid-4'-chloranilide, 4-chloro-3-aminobenzoic acid-2'4'5'-trichloranilide, ...
		A process according to claim 1 wherein the diazotizable amine is selected from the group consisting of 2,4- and 2,5-dichloraniline, ... 2-methoxy-5-methyl-4-aminobenzene sulphonic acid methyl amide, 2,5-dimethoxy-4-aminobenzoic sulphonic acid anilide, 2-methoxy-5-methyl-4-benzoylaminoaniline, 4-ethoxy-3-aminobenzamide, 4-methoxy-3-aminobenzoic acid anilide, 4-methyl-3-aminobenzoic acid-2'4'-dimethylanilide, 4-methyl-3-aminobenzoic acid-4'-chloranilide, 4-chloro-3-aminobenzoic acid-2'-methyl-5'-chloranilide, ...

		Representative compounds of formula (1) that may be employed are: ... N'-n-butyl-3-amino-4-methoxybenzenesulfonamide N'-(gamma-methoxypropyl)-3-amino-4-methoxybenzenesulfonamide N'-methyl-3-amino-4-methoxybenzenesulfonamide 3-amino-4-methoxyphenylbenzylsulfone 3-amino-4-methoxybenzanilide 2-amino-1-phenol-4-sulfonanilide 2-amino-4-(methylsulfonyl)phenol 4-amino-3-hydroxy-4'-chlorobenzenesulfonanilide ...
		Exemplary amines and diamines useful in the invention are: ... 2-aminobenzoic acid 2-trifluoromethylaniline 3-amino-4-methoxybenzanilide

9
[ 120-35-4 ]
[ 169762-05-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; trichlorophosphate; In water; N,N-dimethyl-aniline;	Step A Preparation of 3-Amino-4-methoxy-4'-N,N-Di-methylaminobenzophenone STR262 Fifty grams (0.2 mole) of <strong>[120-35-4]3-amino-4-methoxybenzanilide</strong>, 70 g (0.58 mole) N,N-dimethylaniline and 36 g POCl3 were heated on a water bath at 90 C. to 95 C. for 4 to 6 hours. The product was then cautiously poured into a solution of 23 ml of concentrated hydrochloric acid in 250 ml water. The resulting solution was warmed at 80 C. until the initial reddish color disappeared, indicating that the aniline was completely hydrolyzed. A liter of water was added to precipitate the ketone, which was filtered, washed with cold water, and recrystallized from a 2:1 aqueous alcohol solution. Yield: 38 g of slightly yellowish crystals, metling point 82 C.

References: [1]Patent: US5428163,1995,A .

10
[ 98-88-4 ]
[ 97-00-7 ]
[ 120-35-4 ]

Yield	Reaction Conditions	Operation in experiment
79%		EXAMPLE 5 3-Amino-4-Methoxybenzanilide According to the procedure of Example 1, substituting 135.5 g. of benzoyl chloride for the acetic anhydride used therein, 2,4-dinitrochlorobenzene was converted to 3-amino-4-methoxybenzanilide, in 79% yield.

References: [1]Patent: US4283556,1981,A .

11
[ 120-35-4 ]
[ 23163-86-2 ]
3-[3-(4-Chloro-3-trifluoromethylphenyl)-thioureido]-4-methoxy-N-phenyl-benzamide [ No CAS ]