[ CAS No. 18595-17-0 ] {[proInfo.proName]}

Name: 18595-17-0|Methyl 2-amino-4-methylbenzoate|98%
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Quality Control of [ 18595-17-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 18595-17-0 ]

CAS No. :	18595-17-0	MDL No. :	MFCD09998260
Formula :	C₉H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VAQBJVZNPBNHGC-UHFFFAOYSA-N
M.W :	165.19	Pubchem ID :	11205965
Synonyms :

Calculated chemistry of [ 18595-17-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.09
TPSA :	52.32 Å²

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) :	-5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.96
Log Po/w (XLOGP3) :	2.24
Log Po/w (WLOGP) :	1.37
Log Po/w (MLOGP) :	1.64
Log Po/w (SILICOS-IT) :	1.44
Consensus Log Po/w :	1.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.51
Solubility :	0.507 mg/ml ; 0.00307 mol/l
Class :	Soluble
Log S (Ali) :	-2.97
Solubility :	0.175 mg/ml ; 0.00106 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.49
Solubility :	0.531 mg/ml ; 0.00321 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.22

Safety of [ 18595-17-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18595-17-0 ]

* 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 [ 18595-17-0 ]
Downstream synthetic route of [ 18595-17-0 ]

[ 18595-17-0 ] Synthesis Path-Upstream 1~7

1
[ 67-56-1 ]
[ 1128-47-8 ]
[ 18595-17-0 ]
[ 2305-36-4 ]

Reference： [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 914 - 915

2
[ 67-56-1 ]
[ 2305-36-4 ]
[ 18595-17-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: at 0℃; for 16 h; Reflux Stage #2: With sodium hydrogencarbonate In water	Concentrated sulphuric acid (1 mL) was added to a solution of 2-amino-4-methyl-benzoic acid (1.0 g, 6.62 mmol) in dry methanol (10 mL) at 0° C., and then heated at reflux for 16 hr. The mixture was cooled to room temperature and concentrated in vacuo. The crude compound was diluted with water (25 mL) and basified with sodium bicarbonate (10 mL). The aqueous layer was extracted with ethyl acetate (2*50 mL) and the combined organic layers were washed with water (50 mL), brine (50 mL) and dried over sodium sulfate. The organic layer was concentrated under reduced pressure affording 2-amino-4-methyl-benzoic acid methyl ester (900 mg, 82percent) as yellow liquid.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 963 - 968
[2] Tetrahedron, 2009, vol. 65, # 2, p. 563 - 578
[3] Patent: US2011/160231, 2011, A1, . Location in patent: Page/Page column 10
[4] Chemische Berichte, 1930, vol. 63, p. 1455,1462
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1919 - 1925

3
[ 2305-36-4 ]
[ 18595-17-0 ]

Reference： [1] Patent: US5599814, 1997, A,

4
[ 2305-36-4 ]
[ 18595-17-0 ]

Reference： [1] Patent: US5658858, 1997, A,

5
[ 186581-53-3 ]
[ 2305-36-4 ]
[ 18595-17-0 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036

6
[ 67-56-1 ]
[ 40314-06-5 ]
[ 1153421-34-1 ]
[ 1356116-12-5 ]
[ 18595-17-0 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 3, p. 946 - 949

7
[ 67-56-1 ]
[ 1128-47-8 ]
[ 18595-17-0 ]
[ 2305-36-4 ]

Reference： [1] Angewandte Chemie, 1981, vol. 93, # 10, p. 914 - 915

[ 18595-17-0 ] Synthesis Path-Downstream 1~46

1
[ 18595-17-0 ]
[ 143-33-9 ]
[ 1213767-07-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; water; copper(II) sulfate Diazotization;

Reference： [1]Mayer; Guenther [Chemische Berichte, 1930, vol. 63, p. 1455,1462]

2
[ 112-77-6 ]
[ 18595-17-0 ]
[ 140112-50-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1609 - 1617

3
[ 67-56-1 ]
[ 1128-47-8 ]
[ 18595-17-0 ]
[ 2305-36-4 ]

Reference： [1]Angewandte Chemie,1981,vol. 93,p. 914 - 915

4
[ 18595-17-0 ]
[ 1488-42-2 ]
[ 100038-82-2 ]

Reference： [1]Synthesis,1985,p. 220 - 222

5
[ 18595-17-0 ]
[ 79-30-1 ]
2-Isobutyrylamino-4-methyl-benzoic acid methyl ester [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 675 - 682

6
[ 18595-17-0 ]
3-(3,5-dimethyl-phenyl)-4-hydroxy-7-methyl-1<i>H</i>-quinolin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2615 - 2620

7
[ 18595-17-0 ]
3-(3,5-dimethyl-phenyl)-7-methyl-4-(1-methyl-piperidin-3-ylmethoxy)-1<i>H</i>-quinolin-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2615 - 2620

8
[ 18595-17-0 ]
[ 141541-77-7 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 675 - 682

9
[ 18595-17-0 ]
[ 128936-38-9 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 675 - 682

10
[ 18595-17-0 ]
[ 128936-39-0 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 675 - 682

11
[ 18595-17-0 ]
(2-Chloromethyl-5-methyl-phenyl)-isobutyl-amine; hydrochloride [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1992,vol. 40,p. 675 - 682

12
[ 18595-17-0 ]
[ 86611-41-8 ]

Reference： [1]Synthesis,1985,p. 220 - 222

13
[ 18595-17-0 ]
[ 1035806-04-2 ]

Reference： [1]Synthesis,1985,p. 220 - 222

14
[ 18595-17-0 ]
[ 4316-23-8 ]

Reference： [1]Chemische Berichte,1930,vol. 63,p. 1455,1462

15
[ 18595-17-0 ]
[ 124-63-0 ]
[ 158579-76-1 ]
methyl 4-methyl-2-[N,N-bis(methylsulphonyl]amino]benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; triethylamine; In dichloromethane;	Reference Example 13 Methanesulphonyl chloride (12.2 ml) was added to a stirred, cooled solution of <strong>[18595-17-0]methyl 2-amino-4-methylbenzoate</strong> (10.3 g) and triethylamine (19.5 ml) in dichloromethane while maintaining the temperature below 0 C. The mixture was stirred at room temperature for 4 hours. Hydrochloric acid (2M) was added and the layers were separated. The organic layer was washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give a mixture of methyl 4-methyl-2-[N,N-bis(methylsulphonyl)amino]benzoate and methyl 4-methyl-2-(N-methylsulphonylamino)benzoate (18.26 g) as a yellow solid which was not further purified.
	With hydrogenchloride; triethylamine;	REFERENCE EXAMPLE 25 Methanesulphonyl chloride (12.2 ml) was added to a stirred, cooled solution of <strong>[18595-17-0]methyl 2-amino-4-methylbenzoate</strong> (103 g) and triethylamine (19.5 ml) in dichlorotuethane while maintaining the temperatare below 0 C. The mixture was stirred at room temperature for 4 hours. Hydrochloric acid solution (2M) was added and the layers were separated. The organic layer was washed with water, dried (magnesium sulphate) and filtered. The filtrate was evaporated to dryness to give a mixture of methyl 4-methyl-2-[N,N-bis(methylsulphonyl)amino]benzoate and methyl 4-methyl-2-(N-methylsulphonylamino)benzoate (18.26 g) as a yellow solid which was not further purified.

Reference： [1]Patent: US6323155,2001,B1
[2]Patent: US5658858,1997,A

16
[ 2305-36-4 ]
methyl 3,4-dichloro-2-(N-methyl-N-methylsulphonytamino)-benzoate [ No CAS ]
[ 18595-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane;	REFERENCE EXAMPLE 23 A mixture of 2-amino-4-methylbenzoic acid (15.0 g) and concentrated suiphuric acid (20 ml) was heated under reflux with methanol for 18 hours. After removal of the solvent the residue was dissolved in dichloromethane, basified with sodium carbonate solution and the organic phase was washed with water, dried (anhydrous magnesium sulphate) and the solvent evaporated to give methyl 2-amino-4-methylbenzoate, m.p. 41-43 C. By proceeding in a similar manner the following compounds were prepared from the appropriately substituted starting materials: methyl 3,4-dichloro-2-(N-methyl-N-methylsulphonytamino)-benzoate, NMR 2.95(s,3H), 3.28(s,3H), 3.89(s,3H), 7.5(d,1H), 7.71(d,1H);

Reference： [1]Patent: US5658858,1997,A

17
[ 2305-36-4 ]
[ 18595-17-0 ]

Yield	Reaction Conditions	Operation in experiment
85.7%	In methanol;	b. Methyl 2-amino-4-methylbenzoate A solution of 2-amino-4-methylbenzoic acid (5.20 g, 34.3 mM) in methanol (70 mL) was cooled in an ice bath and saturated with hydrogen chloride gas. The resulting solution was refluxed for 3 hr and the cooled and poured into an excess of saturated aqueous sodium bicarbonate. The resulting mixture was extracted with ethyl acetate and the combined extracts were washed with saturated aqueous sodium bicarbonate and then dried (MgSO4), filtered and concentrated to leave the title amino ester (5.66 g, 85.7%) as a brown oil; MS(CI): 166 (M+H).

Reference： [1]Patent: US5599814,1997,A

18
[ 18595-17-0 ]
[ 147494-06-2 ]

Yield	Reaction Conditions	Operation in experiment
		c. Dimethyl 4-hydroxy-7-methylquinoline-2,3-dicarboxylate Using a procedure similar to that described in Example 3c. except starting with <strong>[18595-17-0]methyl 2-amino-4-methylbenzoate</strong>, the title diester was obtained (81%) as a tan crystalline solid. An analytical sample was obtained by recrystallization from ethyl acetate to give tan crystals, mp 209-211 C.; MS(CI): 276 (M+H). Analysis for C14 H13 NO5: Calculated: C, 61.09; H, 4.76; N, 5.09 Found: C, 61.19; H, 4.91; N, 5.11

Reference： [1]Patent: US5599814,1997,A

19
[ 6298-19-7 ]
2-amino-N-(2-chloro-pyridin-3-yl)-4-methyl-benzamide [ No CAS ]
[ 18595-17-0 ]
[ 118306-19-7 ]

Yield	Reaction Conditions	Operation in experiment
	With conc. sulphuric acid; In thiophene; dichloromethane; toluene;	EXAMPLE C 5,11-Dihydro-9-methyl-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one 127.0 g (0.485 mol) of 2-amino-N-(2-chloro-pyridin-3-yl)-4-methyl-benzamide (m.p. 150-152 C.) prepared analogously to Example A from 2-chloro-3-amino-pyridine and <strong>[18595-17-0]methyl 2-amino-4-methyl-benzoate</strong> (see F. Mayer and R. Schulze, Ber. Dtsch. Chem. Ges. 58, 1465 [1925]) were suspended in 500 ml of sulpholane and after the addition of 1.4 ml of conc. sulphuric acid the suspension was heated for 3 hours to 130 C. with stirring. It was then left to cool to 80 C., 500 ml of toluene were added and the mixture was left to stand overnight at ambient temperature. The crystals formed were suction filtered, suspended in 0.75 liters of dichloromethane, suction filtered once more and thoroughly washed with dichloromethane. After drying in a circulating air dryer, 70.2 g (64% of theory) of very slightly yellow crystals were obtained, m.p. 286-288 C., which were further reacted without any further purification.

Reference： [1]Patent: US4873236,1989,A

20
[ 865190-68-7 ]
[ 18595-17-0 ]
[ 1107664-04-9 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 563 - 578

21
[ 865190-69-8 ]
[ 18595-17-0 ]
[ 1107664-05-0 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 563 - 578

22
[ 22462-26-6 ]
[ 18595-17-0 ]
[ 1107664-03-8 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 5714 - 5718
[2]Tetrahedron,2009,vol. 65,p. 563 - 578

23
[ 4641-57-0 ]
[ 18595-17-0 ]
[ 1042430-76-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2076 - 2084

24
[ 128073-03-0 ]
[ 18595-17-0 ]
[ 929214-89-1 ]

Yield	Reaction Conditions	Operation in experiment
44%	With pyridine; In 1,4-dioxane; at 20℃; for 12h;	Example 29A Methyl 2-[(5-chloropyridin-2-yl)carbonyl]amino}-4-methyl benzoate 234 mg (1.3 mmol, 1.1 eq.) of the compound of Example 2A are added to a solution of 200 mg (1.2 mmol) of <strong>[18595-17-0]methyl 2-amino-4-methylbenzoate</strong> [G. Reissenweber et al., Angew. Chem. 1981, 93, 914-915] in 6 ml of dioxane and 0.25 ml of pyridine. The reaction mixture is stirred at room temperature for 12 h. After addition of water, the precipitate formed is filtered off, washed with diethyl ether and dried under reduced pressure. Yield: 163 mg (44% of theory) LC-MS (Method 3): Rt=2.90 min; MS (ESIpos): m/z=305 [M+H]+.

Reference： [1]Patent: US2010/4292,2010,A1 .Location in patent: Page/Page column 25

25
[ 18595-17-0 ]
C₉H₉N₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1767 - 1770

26
[ 186581-53-3 ]
[ 2305-36-4 ]
[ 18595-17-0 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036

27
[ 18595-17-0 ]
[ 100-52-7 ]
[ 1246775-86-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 7033 - 7036
[2]Journal of the American Chemical Society,2019,vol. 141,p. 6719 - 6725
[3]Chemistry - A European Journal,2019,vol. 25,p. 1727 - 1732

28
[ 18595-17-0 ]
[ 1310327-97-9 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 5714 - 5718

29
[ 18595-17-0 ]
(S)-13-methyl-7,8-dihydrobenzo[d]quinazolo[1,2,3-a,b][1,3]diazonane-1,9,10,16-tetrone [ No CAS ]
(R)-13-methyl-7,8-dihydrobenzo[d]quinazolo[1,2,3-a,b][1,3]diazonane-1,9,10,16-tetrone [ No CAS ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 5714 - 5718

30
[ 75-44-5 ]
[ 18595-17-0 ]
[ 1227375-06-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3358 - 3361

31
[ 18595-17-0 ]
C₁₀H₁₁N₃O₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 3358 - 3361

32
[ 18595-17-0 ]
[ 3288-04-8 ]
2-mercapto-3-(2-methoxy-phenyl)-7-methyl-3H-quinazolin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With acetic acid; In ethanol; for 16h;Reflux;	1-Isothiocyanato-2-methoxy-benzene (0.76 mL, 5.45 mmol) was added to a solution of <strong>[18595-17-0]2-amino-4-methyl-benzoic acid methyl ester</strong> (900 mg, 5.45 mmol) and acetic acid (1.5 mL) in ethanol (10 mL), and heated at reflux for 16 hr. The reaction mixture was cooled to room temperature and diluted with ethanol. The precipitated solid was filtered, washed with ethanol and dried to afford 2-mercapto-3-(2-methoxy-phenyl)-7-methyl-3H-quinazolin-4-one (1.0 g, 62%) as white solid.

Reference： [1]Patent: US2011/160231,2011,A1 .Location in patent: Page/Page column 11

33
[ 67-56-1 ]
[ 40314-06-5 ]
[ 1153421-34-1 ]
[ 1356116-12-5 ]
[ 18595-17-0 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 946 - 949

34
[ 18595-17-0 ]
[ 1551021-81-8 ]