[ CAS No. 18515-67-8 ] {[proInfo.proName]}

Name: 18515-67-8|3-Methyl-4-nitrobenzaldehyde|97%
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Quality Control of [ 18515-67-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 18515-67-8 ]

CAS No. :	18515-67-8	MDL No. :	MFCD08445621
Formula :	C₈H₇NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WHJDQIWWIJARMK-UHFFFAOYSA-N
M.W :	165.15	Pubchem ID :	11194528
Synonyms :

Calculated chemistry of [ 18515-67-8 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.62
TPSA :	62.89 Å²

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) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.2
Log Po/w (XLOGP3) :	2.3
Log Po/w (WLOGP) :	1.72
Log Po/w (MLOGP) :	0.59
Log Po/w (SILICOS-IT) :	0.28
Consensus Log Po/w :	1.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.55
Solubility :	0.464 mg/ml ; 0.00281 mol/l
Class :	Soluble
Log S (Ali) :	-3.26
Solubility :	0.091 mg/ml ; 0.000551 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.11
Solubility :	1.29 mg/ml ; 0.00783 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 18515-67-8 ]

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 [ 18515-67-8 ]

* 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 [ 18515-67-8 ]
Downstream synthetic route of [ 18515-67-8 ]

[ 18515-67-8 ] Synthesis Path-Upstream 1~6

1
[ 18515-67-8 ]
[ 1196-69-6 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 1, p. 137 - 139

2
[ 80866-75-7 ]
[ 18515-67-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridinium chlorochromate In dichloromethane at 20℃; for 3 h;	Step 1: 3-methyl-4-nitrobenzaldehyde: To a solution of (3-methyl-4- nitrophenyl)methanol (1.0 equiv.) in dichoromethane, pyridinium chlorochromate (1.1 equiv.) was added and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered through celite and the filtrate was evaporated. The residue was adsorbed on silica (100-200 mesh) and purified by flash chromatography on silica gel, eluting with 5percent ethyl acetate in petroleum ether (60-80), to provide the title compound in the form of creamish crystals (93percent); ¹H NMR (300 MHz, CDCl₃) δ: 2.66 (s, 3H), 7.84-7.87 (m, 2H), 8.04-8.07 (d, J = 8.7 Hz, IH), 10.12 (s, IH); IR (KBr) 3104, 3079, 2981, 2857, 2743, 1702, 1607, 1518, 1383, 1361, 1308, 1226, 1153, 1008, 832, 735 cm^"1.
58 g	With manganese(IV) oxide In dichloromethane at 40℃; for 2 h;	A flask was charged with (3-methyl-4-nitro-phenyl)-methanol (66.9 g, 0.400 mol), manganese(IV) oxide (85percent, 5 μm powder, 409.1 g, 4.00 mol), and CH₂Cl₂(1337 mL). The mixture was stirred at 40° C. for at least 2 h or until HPLC analysis showed that the reaction had proceeded to greater the 97percent completion. The cooled batch was diluted with CH₂Cl₂(1 L) and filtered through a Celite® pad (34 g), and the filter cake was rinsed with more CH₂Cl₂(1 L). The filtrate and washes were concentrated under in vacuo to dryness to give the title compound as a yellow solid (58 g, 87percent yield).

Reference： [1] Patent: WO2010/23609, 2010, A1, . Location in patent: Page/Page column 117
[2] Chemistry - A European Journal, 2015, vol. 21, # 9, p. 3567 - 3571
[3] European Journal of Organic Chemistry, 2016, vol. 2016, # 20, p. 3401 - 3407
[4] Farmaco, 1999, vol. 54, # 9, p. 579 - 583
[5] Patent: WO2007/24843, 2007, A2, . Location in patent: Page/Page column 63-64
[6] Patent: US2013/310394, 2013, A1, . Location in patent: Paragraph 0153-0154

3
[ 89-87-2 ]
[ 18515-67-8 ]
[ 3113-71-1 ]
[ 80866-75-7 ]

Reference： [1] Patent: CN105237317, 2016, A, . Location in patent: Paragraph 0079; 0080

4
[ 80866-75-7 ]
[ 7529-22-8 ]
[ 18515-67-8 ]

Reference： [1] Patent: US6593335, 2003, B1,

5
[ 3113-71-1 ]
[ 18515-67-8 ]

Reference： [1] Tetrahedron, 2008, vol. 64, # 11, p. 2586 - 2595
[2] Patent: US2013/310394, 2013, A1,

6
[ 89-87-2 ]
[ 18515-67-8 ]

Reference： [1] Monatshefte fuer Chemie, 1912, vol. 33, p. 1267
[2] Journal of the Chemical Society [Section] B: Physical Organic, 1967, p. 1154 - 1158

[ 18515-67-8 ] Synthesis Path-Downstream 1~82

1
[ 89-87-2 ]
[ 18515-67-8 ]

Reference： [1]Monatshefte fur Chemie,1912,vol. 33,p. 1267
[2]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

2
[ 18515-67-8 ]
[ 3113-71-1 ]

Reference： [1]Monatshefte fur Chemie,1912,vol. 33,p. 1267

3
[ 18515-67-8 ]
[ 80866-75-7 ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

4
1-diacetoxymethyl-3-methyl-4-nitro-benzene [ No CAS ]
[ 18515-67-8 ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

5
[ 18515-67-8 ]
[ 99-98-9 ]
[ 112523-38-3 ]

Reference： [1]Polish Journal of Chemistry,1987,vol. 61,p. 589 - 598

6
[ 18515-67-8 ]
[ 36898-64-3 ]

Reference： [1]Roczniki Chemii,1972,vol. 46,p. 179 - 185
[2]Roczniki Chemii,1972,vol. 46,p. 179 - 185

7
[ 18515-67-8 ]
[ 36984-54-0 ]

Reference： [1]Roczniki Chemii,1972,vol. 46,p. 179 - 185

8
[ 80866-75-7 ]
[ 18515-67-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With pyridinium chlorochromate; In dichloromethane; at 20℃; for 3h;	Step 1: 3-methyl-4-nitrobenzaldehyde: To a solution of (3-methyl-4- nitrophenyl)methanol (1.0 equiv.) in dichoromethane, pyridinium chlorochromate (1.1 equiv.) was added and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was filtered through celite and the filtrate was evaporated. The residue was adsorbed on silica (100-200 mesh) and purified by flash chromatography on silica gel, eluting with 5% ethyl acetate in petroleum ether (60-80), to provide the title compound in the form of creamish crystals (93%); 1H NMR (300 MHz, CDCl3) delta: 2.66 (s, 3H), 7.84-7.87 (m, 2H), 8.04-8.07 (d, J = 8.7 Hz, IH), 10.12 (s, IH); IR (KBr) 3104, 3079, 2981, 2857, 2743, 1702, 1607, 1518, 1383, 1361, 1308, 1226, 1153, 1008, 832, 735 cm"1.
	With manganese(IV) oxide; In dichloromethane; at 20℃; for 48h;	Intermediates 25 & 26 To a stirred solution of Intermediate 23 or 24 (60 mmol) in methylene chloride (200 mL) was added manganese oxide (52 g, 600 mmol). The reaction mixture was stirred at room temperature for 2 days and filtered through diatomaceous. The filter cake was washed with methylene chloride (500 mL) and the filtrate was concentrated under reduced pressure to afford the crude aldehyde. To a solution of the aldehyde (8.7 g, 54 mmol) at -78 0C in tetrahydrofuran (180 mL) was added MeLi (2 M in THF, 80 mmol, 40 mL) dropwise via addition funnel. The resulting solution was stirred under nitrogen, at -78 0C, for 4 hours. The reaction mixture was quenched slowly with saturated ammonium chloride solution at -78 0C and warmed to 0 C. The mixture was partitioned between ethyl acetate (500 mL) and water (300 mL). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The crude oil was purified by chromatography (silica gel, 2:1 hexanes/ethyl acetate) to afford the alcohol intermediate. To a stirred solution of EPO <DP n="65"/>the alcohol (4.0 g, 22 mmol) in methylene chloride (75 ml_) was added manganese oxide (26 g, 300 mmol). The reaction mixture was stirred at room temperature for 2 days and then filtered through diatomaceous. The filter cake was washed with methylene chloride (500 ml_) and the filtrate was concentrated under reduced pressure and the resulting solid was purified by chromatography (silica gel, 4:1 hexanes/ethyl acetate).Intermediate 25 (4.3 g, 35% for 3 steps): 1H NMR (500 MHz, CDCI3) .58.01-7.99 (m, 1 H), 7.91 (s, 1 H), 7.89-7.82 (m, 1H), 2.65-2.64 (m, 6H); HPLC >99%, tR = 8.05 min;Intermediate 26 (1.6 g, 24% for 3 steps): 1H NMR (500 MHz, CDCI3) 67.90-7.88 (m, 1 H), 7.68 (s, 1 H), 7.53-7.55 (m, 1 H), 4.01 (s, 3H), 2.65 (s, 3H).
58 g	With manganese(IV) oxide; In dichloromethane; at 40℃; for 2h;	A flask was charged with (3-methyl-4-nitro-phenyl)-methanol (66.9 g, 0.400 mol), manganese(IV) oxide (85%, 5 mum powder, 409.1 g, 4.00 mol), and CH2Cl2 (1337 mL). The mixture was stirred at 40 C. for at least 2 h or until HPLC analysis showed that the reaction had proceeded to greater the 97% completion. The cooled batch was diluted with CH2Cl2 (1 L) and filtered through a Celite pad (34 g), and the filter cake was rinsed with more CH2Cl2 (1 L). The filtrate and washes were concentrated under in vacuo to dryness to give the title compound as a yellow solid (58 g, 87% yield).

Reference： [1]Patent: WO2010/23609,2010,A1 .Location in patent: Page/Page column 117
[2]Chemistry - A European Journal,2015,vol. 21,p. 3567 - 3571
[3]European Journal of Organic Chemistry,2016,vol. 2016,p. 3401 - 3407
[4]Il Farmaco,1999,vol. 54,p. 579 - 583
[5]Patent: WO2007/24843,2007,A2 .Location in patent: Page/Page column 63-64
[6]Patent: US2013/310394,2013,A1 .Location in patent: Paragraph 0153-0154

9
[ 18515-67-8 ]
[ 109-55-7 ]
N,N-dimethyl-N'-(3-methyl-4-nitro-benzylidene)-propane-1,3-diamine [ No CAS ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 579 - 583

10
[ 75-17-2 ]
diazotized 3-methyl-4-nitro-aniline [ No CAS ]
[ 18515-67-8 ]

Reference： [1]Journal of the American Chemical Society,1959,vol. 81,p. 5954,5956 Anm.27

11
[ 18515-67-8 ]
chromic acid [ No CAS ]
[ 3113-71-1 ]

Reference： [1]Monatshefte fur Chemie,1912,vol. 33,p. 1267

12
[ 536-57-2 ]
[ 18515-67-8 ]
[ 77287-34-4 ]
[ 570384-35-9 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

13
[ 18515-67-8 ]
[ 24313-88-0 ]
[1-(3-Methyl-4-nitro-phenyl)-meth-(Z)-ylidene]-(3,4,5-trimethoxy-phenyl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

14
[ 18515-67-8 ]
[ 107-21-1 ]
[ 148582-48-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,2005,vol. 42,p. 137 - 139

15
[ 18515-67-8 ]
[ 1196-69-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,2005,vol. 42,p. 137 - 139

16
[ 18515-67-8 ]
[ 152879-74-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,2005,vol. 42,p. 137 - 139

17
[ 18515-67-8 ]
[ 1026678-47-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,2005,vol. 42,p. 137 - 139

18
[ 18515-67-8 ]
[ 424834-77-5 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

19
[ 18515-67-8 ]
[ 424834-29-7 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

20
[ 18515-67-8 ]
1-methyl-5-[3-(3,4,5-trimethoxy-phenyl)-3H-imidazol-4-yl]-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

21
[ 18515-67-8 ]
[ 424834-30-0 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

22
[ 18515-67-8 ]
1-methyl-4-(N-methyl-indol-5-yl)-5-(3,4,5-trimethoxyphenyl)imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

23
[ 18515-67-8 ]
1-methyl-5-[3-(3,4,5-trimethoxy-phenyl)-3H-imidazol-4-yl]-2,3-dihydro-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

24
[ 18515-67-8 ]
[ 424834-55-9 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

25
[ 18515-67-8 ]
5-[1-methyl-5-(3,4,5-trimethoxy-phenyl)-1H-imidazol-4-yl]-1H-indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 1697 - 1711

26
[ 18515-67-8 ]
[ 756463-30-6 ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 579 - 583

27
[ 18515-67-8 ]
2-(4-amino-3-methyl-phenyl)-3-(3-dimethylamino-propyl)-thiazolidin-4-one [ No CAS ]

Reference： [1]Il Farmaco,1999,vol. 54,p. 579 - 583

28
[ 18515-67-8 ]
trans-3,3'-Dimethyl-4,4'-dinitro-stilben [ No CAS ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

29
[ 18515-67-8 ]
[ 18515-14-5 ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

30
[ 18515-67-8 ]
[ 18515-23-6 ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

31
[ 18515-67-8 ]
Bis-<3-methyl-4-nitro-benzyl>-ether [ No CAS ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

32
[ 18515-67-8 ]
[ 18515-25-8 ]

Reference： [1]Journal of the Chemical Society B: Physical Organic,1967,p. 1154 - 1158

33
[ 1284261-82-0 ]
[ 18515-67-8 ]
[ 763129-65-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; In methanol; at 0 - 20℃; for 10h;	Methanol solution (5 ml) of 3-METHYL-4-NITROBENZALDEHYDE (0.9 g) was added to a methanol suspen- sion (5 ml) of glycine ethyl ester acetate (1.1 g) and sodium cyanotrihydroborate (0.53 g) at 0oC. After stirring the mixture at room temperature for 10 hours, 2N hydrochloric acid (10 ml) and ethyl acetate (10 ml) were added thereto. After removing the organic layer, 1N aqueous solution of sodium hydroxide, (30 ml) was added to the aqueous layer and extracted with ethyl acetate. After washing the organic layer with a saturated aqueous solution of sodium chloride (20 ml), it was dried with anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the obtained residue was purified by silica gel column chromatography to obtain the objected ethyl (3-methyl-4- nitrobenzylamino) acetate [0.9 G, H NMR (CDCL3, ppm) ; 1.2 (3H, t), 2.6 (3H, s), 3.4 (2H, s), 3.9 (2H, s), 4.2 (2H, q), 4.8 (2H, s), 7.2-8. 1 (3H, M)].

Reference： [1]Patent: WO2004/80984,2004,A1 .Location in patent: Page 71

34
9-(3-methyl-4-nitrophenyl)-2,3,5.6,7,9-hexahydrothieno[3.2-b]quinolin-8(4H)-one 1,1-dioxide 3-Methyl-4-nitrobenzaldehyde [ No CAS ]
[ 80866-75-7 ]
[ 7529-22-8 ]
[ 18515-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	silica gel; In tetrapropylammonium perruthennate; dichloromethane;	EXAMPLE 219A 3-methyl-4-nitrobenzaldehyde To a solution of 3-methyl-4-nitrobenzyl alcohol (3.0 g, 18 mmol), N-methylmorpholine-N-oxide (3.2 g, 27 mmol), and powdered 4A molecular sieves (8.98 g) in methylene chloride (40 mL) was added in one portion tetrapropylammonium perruthenate (0.315 g, 0.898 mmol), and the reaction stirred at room temperature. The reaction was filtered through silica gel, eluding with methylene chloride, solvent evaporated and the residue purified by flash chromatography to provide 2.2 g of the title compound. Examp~le 219B 5 9-(3-methyl-4-nitrophenyl)-2,3,5.6,7,9-hexahydrothieno[3.2-b]quinolin-8(4H)-one 1,1-dioxide 3-Methyl-4-nitrobenzaldehyde (0.99 g, 6.0 mmol) was processed according to the method of Example 11 5C to provide the title compound. mp >250; 10 1H NMR (DMSO-d6) delta 1.90 (m, 2H), 2.26 (m, 2H), 2.54 (m, 2H), 2.86 (m, 1H), 3.02 (m, 1H), 3.38 (m, 2H), 4.98 (s, 1H), 7.30 (m, 2H), 7.92 (d, 1H, J=6.0Hz)), 9.85 (s, 1H); MS (ESI+) m/z 375 (M+H)+; Anal. Calcd for C18H18N205S0.2H20: C, 57.74;H, 4.85; N, 7.48. Found: C, 56.91;H, 5.07; N, 7.07.

Reference： [1]Patent: US6593335,2003,B1

35
[ 18515-67-8 ]
[ 917-54-4 ]
[ 866639-01-2 ]

Yield	Reaction Conditions	Operation in experiment
		Intermediates 25 & 26 To a stirred solution of Intermediate 23 or 24 (60 mmol) in methylene chloride (200 mL) was added manganese oxide (52 g, 600 mmol). The reaction mixture was stirred at room temperature for 2 days and filtered through diatomaceous. The filter cake was washed with methylene chloride (500 mL) and the filtrate was concentrated under reduced pressure to afford the crude aldehyde. To a solution of the aldehyde (8.7 g, 54 mmol) at -78 0C in tetrahydrofuran (180 mL) was added MeLi (2 M in THF, 80 mmol, 40 mL) dropwise via addition funnel. The resulting solution was stirred under nitrogen, at -78 0C, for 4 hours. The reaction mixture was quenched slowly with saturated ammonium chloride solution at -78 0C and warmed to 0 C. The mixture was partitioned between ethyl acetate (500 mL) and water (300 mL). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The crude oil was purified by chromatography (silica gel, 2:1 hexanes/ethyl acetate) to afford the alcohol intermediate. To a stirred solution of EPO <DP n="65"/>the alcohol (4.0 g, 22 mmol) in methylene chloride (75 ml_) was added manganese oxide (26 g, 300 mmol). The reaction mixture was stirred at room temperature for 2 days and then filtered through diatomaceous. The filter cake was washed with methylene chloride (500 ml_) and the filtrate was concentrated under reduced pressure and the resulting solid was purified by chromatography (silica gel, 4:1 hexanes/ethyl acetate).Intermediate 25 (4.3 g, 35% for 3 steps): 1H NMR (500 MHz, CDCI3) .58.01-7.99 (m, 1 H), 7.91 (s, 1 H), 7.89-7.82 (m, 1H), 2.65-2.64 (m, 6H); HPLC >99%, tR = 8.05 min;Intermediate 26 (1.6 g, 24% for 3 steps): 1H NMR (500 MHz, CDCI3) 67.90-7.88 (m, 1 H), 7.68 (s, 1 H), 7.53-7.55 (m, 1 H), 4.01 (s, 3H), 2.65 (s, 3H).

Reference： [1]Patent: WO2007/24843,2007,A2 .Location in patent: Page/Page column 63-64

36
[ 18515-67-8 ]
[ 172542-26-6 ]
[ 943964-03-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	With hydrogenchloride; In water; toluene; at 20℃; for 24h;	Example 1; (5RS.7S)-7-Methyl-5-(3-methyl-4-nitrophenyl)-7,8-dihvdro- 5H-1.3-dioxolor4.5-q1 izochromane (XII)To the solution of 20.0 g (110.9 rmoles) of (S)-alpha-methy.-1,3- benzodioxol-5-ethanol and 18.31 g (110.9 mmoles) of 3- methyl-4-nitrobenzaldehyde in 220 ml of toluene 16.2 ml (200 mmoles) of concentrated hydrochloric acid are added. The mixture is stirred for 24 hours at room temperature. The precipitated crystals are filtered, and washed with 3x30ml of toluene, 3x30ml of water, then 20 ml of ethanol. The filtrate is washed with 200 ml of water, 100 ml of saturated sodium carbonate solution then with 3x100 ml of water, dried over anhydrous sodium sulphate, then evaporated. The residue is combined with the crystals which are filtered from the reaction mixture and dissolved in 400 ml of hot ethanol, then crystallised for 16 hours at room temperature. The precipitated crystals are filtered and washed with 3x30 ml of ethanol.Thus, the yield is 21.35 g (59 %) of the title product. Melting point: 150-152 0C.[alpha]20D= +29.2 (C=I1 CHCI3)IR (KBr): 1483, 1360, 1241, 1038. cm'1 <n="58"/>1H-NMR (CDCI3): 7.96 (d, J=9.0 Hz, 1H), 7.31 (m, 2H), 6.59 (s, 1H)1 6.07 (s, 1H), 5.87 (d, J=1.4 Hz, 1H), 5.85 (d, J=1.4 Hz, 1H), 5.66 (s, 1H), 3.97 (m, 1 H), 2.82 (dd, J1=10.9 Hz es J2=16.0 Hz, 1H), 2.68 (dd, J1= 1.9Hz es J2=16.1 Hz, 1 H), 2.59 (S, 3H), 1.38(d, J=6.1 Hz, 3H) ppm.13C-NMR (CDCI3): 148.71 , 147.67, 146.54, 146.05, 134.05, 132.82, 129.40, 127.21, 127.06, 124.99, 108.31, 106.08, 100.85, 79.84, 71.40, 36.31 , 21.65, 20.55. ppm.

Reference： [1]Patent: WO2007/77469,2007,A1 .Location in patent: Page/Page column 55-56

37
[ 565176-99-0 ]
[ 18515-67-8 ]
[ 943964-12-3 ]

Yield	Reaction Conditions	Operation in experiment
21.2%	With hydrogenchloride; zinc(II) chloride; In benzene; for 6.5h;Heating / reflux;	Example 11; (1/?S,3S)-7-Chloro-3-methyl-1-(3-methyl-4-nitrophenyl)- izochromane (XII)To the solution of 8.9 g (52.0 mmol) of (S)-(+)-1-(4- chlorophenyl)-2-propanol and 8.58 g (52.0 mmol) of 3- methyl-4-nitrobenzaldehyde in 80 ml of anhydrous benzene 10.63 g (78.0 mmol) of powdered melting dried anhydrous zinc chloride are added, then dry hydrochloric acid gas is introduced to the reaction mixture for five hours under vigorous stirring. Then the reaction mixture is refluxed for 1.5 hours. The organic layer is decanted from the deliquescing zinc chloride layer, then the organic layer is stirred with 3x80 ml of toluene. The collected organic layers are combined and washed with 5x80 ml of 25% aqueous sodium bisulphite <n="71"/>solution, 80 ml of saturated sodium hydrogen carbonate solution, 3x80 ml of water, dried over sodium sulphate then evaporated. The residue is dissolved in 15 ml of hot ethanol and kept for 16 hours in refrigerator. The precipitated crystals are filtered and washed with 3x5 ml of ethanol. Thus, the yield is 3.51 g (21.2 %) of the desired product. The melting point is 142-147 0C.[alpha]D20= +43.91 (c=0.5, CHCI3), [alpha]43620=+120.76 (c=0.5,CHCI3)IR (KBr): 1518, 1342, 1075 cm"1.1H-NMR (CDCI3): 7.98 (m, 1H), 7.31 (m, 2H), 7.15 (dd,J1=2.1 Hz, J2=8.2 Hz, 1H), 7.08 (d, J=8.2 Hz1 1H), 6.60 (d,J=1.6 Hz, 1H), 5.70 (s, 1H), 4.00 (m, 1H), 2.85 (dd, J1=10.7Hz, J2=16.4 Hz, 1H), 2.78 (dd, J1=2.9 Hz es J2=16.0 Hz,1 H), 2.61 (s, 3H), 1.40 (d, J=6.1 Hz, 3H) ppm.13C-NMR (CDCI3): 146.73, 138.30, 134.22, 132.90, 132.38,131.83, 130.15, 127.28, 127.13, 126.08, 125.15, 79.59,71.51 , 35.69, 21.72, 20.60 ppm.

Reference： [1]Patent: WO2007/77469,2007,A1 .Location in patent: Page/Page column 68-69

38
[ 565176-98-9 ]
[ 18515-67-8 ]
[ 943964-13-4 ]

Yield	Reaction Conditions	Operation in experiment
21.5%	With hydrogenchloride; zinc(II) chloride; In benzene; for 6.5h;Heating / reflux;	Example 12; (1ftS,3/?)-7-Chloro-3-methyl-1-(3-methyl-4-nitrophenyl)- izochromane (XII)To the solution of 8.53 g (50.0 mmol) of (/?)-(-)- 1 -(4- chlorophenyl)-2-propanol and 8.25 g (50.0 mmol) of 3- methyl-4-nitrobenzaldehyde in 80 ml of anhydrous benzene, <n="72"/>10.22 g (75.0 mmol) of powdered, melting dried anhydrous zinc chloride is added , then dry hydrochloric acid gas is introduced to the reaction mixture for five hours under vigorous stirring.Then the reaction mixture is refluxed for 1.5 hours. The organic layer is decanted from the deliquescing zinc chloride layer , then the organic layer is stirred with 3x80 ml of toluene.The collected organic layers are combined, washed with5x80 ml of 25% aqueous sodium bisulphite solution, 80 ml of saturated sodium hydrogen carbonate solution, 3x80 ml of water, dried over sodium sulphate, then evaporated.The residue is dissolved in 15 ml of hot ethanol and kept for16 hours in refrigerator. The precipitated crystals are filtered and washed with 3x5 ml of ethanol.Thus, the yield is 3.42 g (21.5 %) of the desired product. The melting point is 141-144 0C.[alpha]D20= -43.19 (c=0.5, CHGI3)IR (KBr): 1518, 1342, 1075 cm'1.1H-NMR (CDCI3): 7.98 (m, 1 H), 7.31 (m, 2H)1 7.15 (dd,J1=2.1 Hz, J2=8.2 Hz, 1H), 7.08 (d, J=8.2 Hz, 1H), 6.60 (d,J=1.6 Hz, 1H), 5.70 (s, 1H), 4.00 (m, 1 H), 2.85 (dd, J1=10.7Hz, J2=16.4 Hz, 1H), 2.78 (dd, J1=2.9 Hz es J2=16.0 Hz,1H), 2.61 (S, 3H), 1.40 (d, J=6.1 Hz, 3H) ppm. <n="73"/>13C-NMR (CDCI3): 146.73, 138.30, 134.22, 132.90, 132.38, 131.83, 130.15, 127.28, 127.13, 126.08, 125.15, 79.59, 71.51, 35.69, 21.72, 20.60 ppm.

Reference： [1]Patent: WO2007/77469,2007,A1 .Location in patent: Page/Page column 69-71

39
[ 578-57-4 ]
[ 18515-67-8 ]
[ 1018668-98-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 2586 - 2595

40
[ 3113-71-1 ]
[ 18515-67-8 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 2586 - 2595
[2]Patent: US2013/310394,2013,A1

41
[ 18515-67-8 ]
[ 1210757-60-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydroxylamine hydrochloride; In methanol; at 65℃; for 2h;	Step 2: (Zzeta)-<strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> oxime: To a warm solution of 3-methyl-4- nitrobenzaldehyde (1.0 equiv.) in methanol was added hydroxylamine hydrochloride (2.0 equiv.) and the mixture was stirred at 65 0C for 2 hours. Methanol was evaporated and the residue was diluted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SOzJ, filtered and concentrated in vacuo. The residue was then recrystallized from ethyl acetate and petroleum ether 60-80, to provide the title compound as a creamish solid (81%); 1H NMR (300 MHz, CDCl3) delta: 2.62 (s, 3H), 7.54-7.56 (m, 2H), 7.89 (s, IH), 7.98- 8.01 (d, J = 9.0 Hz, IH), 8.14 (s, IH); IR (KBr) 3375, 3207, 3087, 2994, 1607, 1585, 1506, 1384, 1319, 1161, 986, 841, 755 cm"1.
	With hydroxylamine hydrochloride; sodium acetate; In ethanol; at 20℃; for 2h;Inert atmosphere;	Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed 3 -methyl -4- nitrobenzaldehyde (5 g, 30.28 mmol, 1.00 equiv), ethanol (100 mL), AcONa (5 g, 2.00 equiv) and NH2OH.HCI (3.2 g, 1.50 equiv). The resulting solution was stirred for 2 h at room temperature. The resulting solution was concentrated under vacuum and then diluted with 100 ml of water. The resulting mixture was extracted with 2x200 mL of ethyl acetate. The organic layers were combined and washed with 3x100 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 5.5 g (crude) of (E)-N-[(3-methyl-4- nitrophenyl)methylidene]hydroxylamine as a yellow solid. MS (ESI, m/z): 181 [M+H]+.

Reference： [1]Patent: WO2010/23609,2010,A1 .Location in patent: Page/Page column 117
[2]Patent: WO2019/36407,2019,A1 .Location in patent: Page/Page column 142

42
[ 18515-67-8 ]
[ 4943-86-6 ]
[ 1235480-98-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With copper dichloride; In ethanol; for 3.5h;Reflux;	Example 73. Preparation of 3-(4-chlorophenyl)-2-(1 H-indol-5-yl)quinazolin-4(3H)- one; [0265] <strong>[18515-67-8]3-methyl-4-nitro-benzaldehyde</strong> (0.268 g, 1.60 mmol) and anyhydrous CuCb (0.437 g, 3.20 mmol) were added to a solution of 2-amino-Lambda/-(4- chlorophenyl)benzamide (0.400 g, 1.60 mmol) in anyhydrous EtOH (15 ml_) and heated at reflux temperature for 3.5 hours. After concentration in vacuo and dissolving the residue in EtOAc, the organics were washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 70% EtOAc in heptane, afforded 3-(4-chlorophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3H)-one (0.300 g, 48%).[0266] te/t-butoxybis(dimethylamino)methane (0.47 ml_, 2.30 mmol) was added to a solution of 3-(4-chlorophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3/-/)- one (0.300 g, 0.76 mmol) in DMF (30 ml_). After heating at 400C for 3.5 hours, concentration in vacuo afforded (£)-3-(4-Chlorophenyl)-2-(3-(2- (dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3H)-one (0.342 g, 100%).[0267] Zn dust (0.220 g, 3.35 mmol) was added to a solution of (E)-3-(4- chlorophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3/-/)-one in AcOH (15 ml_). After heating and stirring at reflux temperature for 4 hours, the mixture was basified with 1 N NaOH and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 90% EtOAc in heptane, afford the title compound as a white solid (0.048 g, 39%). 1H-NMR (300 MHz, DMSO-de): delta 11.19 (s, 1 H), 8.18-8.21 (m, 1 H), 7.88-8.00 (m, 1 H), 7.75 (d, J = 7.7 Hz, 1 H), 7.47-7.70 (m, 2H), 7.30-7.44 (m, 5H), 7.20 (d, J = 8.4 Hz, 1 H), 7.06 (d, J = 6.8 Hz, 1 H), 6.40 (d, J = 2.0 Hz, 1 H). MS (APCI) m/z: 372 (M+H)+.

Reference： [1]Patent: WO2010/79431,2010,A2 .Location in patent: Page/Page column 113-114

43
[ 50735-55-2 ]
[ 18515-67-8 ]
[ 1235481-08-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With copper dichloride; In ethanol; for 3.5h;Reflux;	Example 80. Preparation of 3-(4-(dimethylamino)phenyl)-2-(1 H-indol-5-yl)quinazolin- 4(3H)-one; [0282] <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> (0.85 g, 5.20 mmol) and anhydrous CuCI2 (2.1 g, 15.5 mmol) were added to a solution of 2-amino-Lambda/-(4- bromophenyl)benzamide (1.5 g, 5.20 mmol) in anhydrous EtOH (60 ml_). After heating at reflux temperature for 3.5 hours, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with H2O, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 15% to 60% EtOAc in heptane, afforded 3-(4-bromophenyl)-2-(3- methyl-4-nitrophenyl)quinazolin-4(3/-/)-one (1.4 g, 62%).[0283] te/t-Butoxybis(dimethylamino)methane (2.0 mL, 9.60 mmol) was added to a solution of 3-(4-bromophenyl)-2-(3-methyl-4-nitrophenyl)quinazolin-4(3H)- one (1.4 g, 3.20 mmol) in DMF (30 mL). Stirring at 600C for 2 hours and concentrating in vacuo afforded (£)-3-(4-bromophenyl)-2-(3-(2-(dimethylamino)vinyl)- 4-nitrophenyl)quinazolin-4(3H)-one (1.5 g, quantitative).[0284] Zn dust (2.0 g, 30.0 mmol) was added to a solution of (£)-3-(4- bromophenyl)-2-(3-(2-(dimethylamino)vinyl)-4-nitrophenyl)quinazolin-4(3/-/)-one (1.5 g, 3.0 mmol) in AcOH (25 mL). The mixture was stirred at room temperature overnight, then heated to reflux temperature for 1 hour. After cooling to 00C, the reaction mixture was basified with 1 N NaOH and extracted with EtOAc. The organics were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 0% to 40% EtOAc in CH2CI2, afforded 3-(4-bromophenyl)-2-(1/-/-indol-5-yl)quinazolin-4(3H)-one (0.225 g, 18%).[0285] BoC2O (0.142 g, 0.65 mmol) and DMAP (0.6 mg, 0.005 mmol) were added to a solution of 3-(4-bromophenyl)-2-(1H-indol-5-yl)quinazolin-4(3/-/)-one (0.225 g, 0.54 mmol) in THF (15 mL). After stirring at room temperature for 4 hours, the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 10% to 60% EtOAc in hexanes, afforded terf-butyl 5-(3-(4- bromophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-1 H-indole-1 -carboxylate (0.225 g, 81%). [0286] Dimethylamine (0.3 ml_, 0.58 mmol) was added to a solution of tert- butyl 5-(3-(4-bromophenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)-1 H-indole-1 - carboxylate (0.200 g, 0.38 mmol), NafOBu (0.112 g, 1.20 mmol), Pd(OAc)2 (0.013 g, 0.06 mmol) and (J-Bu)3PHBF4 (0.034 g, 0.12 mmol) were added to toluene (5 mL). The mixture was microwaved at 300 W (max. power) and 900C for 30 min, before the mixture was concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 20% to 60% EtOAc in hexanes, afforded the title compound as a brown-yellow solid (0.048 g, 33%). 1H-NMR (300 MHz, DMSO-d6): delta 11.14 (s, 1 H), 8.16 (d, J = 7.7 Hz, 1 H), 7.83-7.88 (m, 1 H), 7.67-7.73 (m, 2H), 7.52-7.57 (m, 1 H), 7.33 (s, 1 H), 7.18 (d, J = 8.7 Hz, 1 H), 7.03-7.08 (m, 3H), 6.54 (d, J = 8.8 Hz, 2H), 6.39 (s, 1H), 2.83 (s, 6H). MS (APCI) m/z: 381 (M+H)+.

Reference： [1]Patent: WO2010/79431,2010,A2 .Location in patent: Page/Page column 120-122

44
[ 18515-67-8 ]
[ 1207090-94-5 ]
[ 1207090-95-6 ]

Yield	Reaction Conditions	Operation in experiment
		SYNTHESIS EXAMPLE 92-2 To a THF solution (40 mL) of 3-(pentafluoroethyl)-1-(pyrrolidin-1-ylmethyl)-1H-pyrazole (2.69 g), 15% n-butyllithiumhexane solution (6.8 mL) was added dropwise at -60 C. or lower, and the mixture was stirred at -70 C. or lower for 2 hours. Subsequently, a THF solution (20 mL) of <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> (1.82 g) was added at -70 C. over 30 minutes, and was stirred at -70 C. for additional 30 minutes. After removing the dry ice bath, the mixture was gradually returned to room temperature with stirring for 4 hours. 2N hydrochloric acid was added to the mixture, which was then extracted with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off, and the crude product was subjected to silica gel column chromatography (mixed solvent of n-hexane and ethyl acetate) to obtain (3-methyl-4-nitrophenyl)[3-(pentafluoroethyl)-1H-pyrazol-5-yl]methanol (1.30 g). 1H-NMR (CDCl3, delta ppm): 1.42 (1H, s), 2.61 (3H, s), 6.02 (1H, s), 6.30 (1H, s), 7.31-7.43 (2H, m), 8.00 (1H, d).

Reference： [1]Patent: US2011/184188,2011,A1 .Location in patent: Page/Page column 103

45
[ 18515-67-8 ]
2-(4-amino-3-methylphenyl)propane-1,3-diamine [ No CAS ]

Reference： [1]Patent: US2013/310394,2013,A1

46
[ 18515-67-8 ]
3-(4-amino-3-methylphenyl)-2,3,4,7-tetrahydro-6H-pyrimido[1,2-c]quinazolin-6-one [ No CAS ]

Reference： [1]Patent: US2013/310394,2013,A1

47
[ 75-52-5 ]
[ 18515-67-8 ]
2-methyl-1-nitro-4-(2-nitro-1-nitromethylethyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36 g	With aluminum oxide; at 100℃; for 3h;	Crude <strong>[18515-67-8]3-methyl-4-nitro-benzaldehyde</strong> (57.8 g, 0.35 mol), basic aluminum oxide (71.4 g, 0.700 mol), and nitromethane (427.3 g, 379 mL, 7.00 mol) were charged to a flask. The mixture was stirred at 100 C. for >3 h or until HPLC analysis showed that the reaction had proceeded to greater the 97% completion. The cooled reaction mixture was filtered through a celite pad (29 g) and the filter cake rinsed with CH2Cl2 (1.2 L). The filtrate and wash were concentrated under reduced pressure to dryness at 50 C. The residue was dissolved in acetone (1.2 L) and treated with charcoal (29 g) with stirring at 50 C. for at least 1 h. The slurry was filtered through a celite pad (29 g) and the filter cake was rinsed with acetone (1.2 L). The filtrate and wash were concentrated to dryness in vacuo. The concentrated product (48 g, 51% mass recovery) was dissolved in ethyl acetate (120 mL) at 75 C. and hexane (400 mL) was added drop-wise at 60-75 C. to induce crystallization. The resulting suspension was filtered at 20-25 C. to give the title compound as a yellow solid (36 g, 38% yield).

Reference： [1]Patent: US2013/310394,2013,A1 .Location in patent: Paragraph 0155-0156

48
[ 18515-67-8 ]
1-[2-(4-amino-piperidin-1-yl)-ethyl]-7-methoxy-1H-quinoxalin-2-one hydrochloride [ No CAS ]
[ 1598417-05-0 ]

Yield	Reaction Conditions	Operation in experiment
0.025 g		To a stirred solution of compound 26g (0.2g,0.66mmol) and <strong>[18515-67-8]3-methyl-4-nitro-benzaldehyde</strong> (0.13 lg, 0.794mmol) in ethanol (4ml) was added titanium isopropoxide (0.2ml) at 0C and stirred. The reaction was gradually brought to RT and stirred for 16h. Then sodiumborohydride (0.049g, 1.34mmol) was added followed by catalytic amount of acetic acid and stirred for 3h at ambient temperature. Upon completion, the solvents in the reaction were distilled out. The crude was diluted with 5% MeOH-CH2Cl2 solution and washed with water. The organic layer was then dried over sodium sulfate and concentrated under reduced pressure. The obtained crude was purified by 100-200mesh-silicagel column chromatography, eluting the required compound with 7% MeOH-CH2Ci2. The obtained compound (0.025g) was confirmed to be the product by mass spectra and 'H-NMR. 1HNMR(400MHz, CDC13) delta 8.19(s, 1H), 7.94(d, 1H), 7.78(d, 2H), 7.34(s, 1H), 7.19(s, 1H), 6.95(d, 1H), 4.03(s, 3H), 3.85(s, 1H), 3.65(s, 2H), 3.23(t, 2H), 3.46(t, 2H),2.95(s,3H), 2.60(d,2H), 2.73-2.77(m, 2H), 1.42(t, 4H). Mass spectra \| M I i \| m/z 452.3

Reference： [1]Patent: WO2014/57415,2014,A2 .Location in patent: Page/Page column 46-47

49
[ 18515-67-8 ]
[ 1598417-38-9 ]
6-methoxy-4-(2-((1R,5S)-3-(4-methyl-3-nitrobenzylamino)-8-azabicyclo[3.2.1]octan-8-yl)ethyl)quinoline-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12 mg	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 0 - 20℃; for 4h;	To a stirred solution of compound lb (0.25g, 0.854mmol) in 1 ,2-Dichloroethane was added 3- methyl-4-nitrobenzaldehyde (0.118g, 0.653mmol), followed by sodium triacetoxy borohydride(0.166g,0.783mmol) and catalytic acetic acid at 0C. The reaction was brought to RT and stirred for 4h. Upon completion the the sovent in the reaction was distilled out. The crude was partitioned between water and 5% MeOH-CH2Cl2. The organic layers were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by silicagel preparative TLC eluting with 5% MeOH-CH2Cl2 to afford the required compound VT-03- 00069(12mg). 1HNMR(400MHz, CDC13) delta 8.91(s,lH), 8.25(s,lH), 8.18(s,lH), 8.06(d,lH), 7.91(dd,lH), 7.42(dd,2H), 4.02(s,3H), 3.62(m, 1H), 3.49-3.51(m ,4H), 3.36(s, 2H), 2.79(t,2H), 2.60(s, 3H), 2.21-2.24(m, 4H), 2.01-2.03(m,2H), 1.56(d,2H). Mass spectra [M+H]+ m/z 486.7

Reference： [1]Patent: WO2014/57415,2014,A2 .Location in patent: Page/Page column 49

50
[ 18515-67-8 ]
4-(1H-imidazol-2-yl)-2-methylaniline [ No CAS ]

Reference： [1]Patent: US9138427,2015,B2

51
[ 18515-67-8 ]
ethyl 3-(1-(4-(1H-imidazol-2-yl)-2-methylphenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl)propanoate [ No CAS ]

Reference： [1]Patent: US9138427,2015,B2

52
[ 18515-67-8 ]
3-(1-(4-(1H-imidazol-2-yl)-2-methylphenyl)-5-(4-methoxyphenyl)-1H-pyrrol-2-yl)propanoic acid [ No CAS ]

Reference： [1]Patent: US9138427,2015,B2

53
[ 18515-67-8 ]
2-methyl-4-(oxazol-2-yl)aniline [ No CAS ]

Reference： [1]Patent: US9138427,2015,B2

54
[ 131543-46-9 ]
[ 18515-67-8 ]
2-(3-methyl-4-nitrophenyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With ammonia; In tetrahydrofuran; methanol; water; at 0 - 20℃;	Step 1: Synthesis of 2-(3-methyl-4-nitrophenyl)-1H-imidazole To a solution of <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> (1.00 g, 6.06 mmol) in THF (6 mL) was added conc. NH3 (4 mL), MeOH (5 mL) and 40% glyoxal (1.32 g, 9.09 mmol) at 0 C. The resulting mixture was stirred overnight at room temperature and evaporated under reduced pressure. The residue was rinsed with water (100 mL) and then purified by silica gel column chromatography (PE:EA=3:1) to afford 2-(3-methyl-4-nitrophenyl)-1H-imidazole as a brown solid (295 mg, 24%).

Reference： [1]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 285

55
[ 18515-67-8 ]
[ 645-36-3 ]
2-(3-methyl-4-nitrophenyl)oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%		Step 1: Synthesis of 2-(3-methyl-4-nitrophenyl)oxazole A mixture of <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> (500 mg) and diethyl aminoacetal (404 mg, 3.03 mmol) was heated at 115 C. for 3 h. After cooling to room temperature, conc. H2SO4 (4.2 mL) was added by one portion and the mixture of P2O5 (1.44 g, 10.15 mmol) and H2SO4 (0.5 mL) was dropped into within 5 min. The resulting mixture was heated at 180 C. for 20 min and then poured into ice-water (100 mL), which was neutralized with ammonia. A precipitate was filtered and purified by prep-TLC (PE:EA=4:1) to afford 2-(3-methyl-4-nitrophenyl)oxazole as a white solid (91 mg, 14%).

Reference： [1]Patent: US9138427,2015,B2 .Location in patent: Page/Page column 285-286

56
[ 89-87-2 ]
[ 18515-67-8 ]
[ 3113-71-1 ]
[ 80866-75-7 ]

Yield	Reaction Conditions	Operation in experiment
		Adding a time fresh material of the oxidation reactor 2,4-dimethyl-nitrobenzene and catalyst is dissolved in the acetic acid CeO2, naphthenic acid cobalt and having the general formula (IV) of a metal phthalocyanine structure (R1=H, R2=CH3CH2, M=Mn) mixture, the total concentration of 450 ppm, acetic acid and 2,4-dimethylnitro Benzene mass ratio of 0. 08. When the device was operated stably, the flow rate of the fresh material in the oxidation reactor was 6.0 mL / h. The average residence time of the oxidation reactor in liquid phase was 5.0 h, and the mass fraction of oxygen was 80% oxygen-enriched air was continuously fed into the oxidation reactor, maintaining the reaction temperature at 125 C and the reaction pressure at 0.6 MPa. The volume ratio of the water added into the hydrolysis reactor to the oxidation reaction liquid entering the hydrolysis reactor is 0.43: 1, and the oxygen-enriched air with the oxygen mass percentage of 80% is continuously fed, and the reaction temperature in the hydrolysis reactor is maintained at 78 C, the reaction pressure is 0. 4MPa, then the hydrolysis reactor liquid phase residence time of 5. Oh. Hydrolysis reactor out The liquid-liquid phase was continuously fed into the liquid-liquid delaminator at a temperature of 45. 8 C and a pressure of 0.3 MPa. The conversion of 2,4-dimethylnitrobenzene in the system was 97.0%, The selectivities of 3-methyl-4-nitrobenzyl alcohol, 3-methyl-4-nitrobenzaldehyde and 3-methyl-4-nitrobenzoic acid were 54.2%, 36.5% 9.3%, other by-products were not detected.

Reference： [1]Patent: CN105237317,2016,A .Location in patent: Paragraph 0079; 0080

57
[ 18515-67-8 ]
1-(4-amino-3-methylphenyl)-2, 2,2-trifluoroethanol [ No CAS ]

Reference： [1]Patent: US2017/217888,2017,A1

58
[ 18515-67-8 ]
4-(1-[dimethyl(2-methyl-2-propanyl)silyl]oxy}-2,2,2-trifluoroethyl)-2-methylaniline [ No CAS ]

Reference： [1]Patent: US2017/217888,2017,A1

59
[ 18515-67-8 ]
1-[2-methyl-4-(2,2,2-trifluoro-1-hydroxyethyl)phenyl]-3-[5-(trifluoromethyl)-2-pyridinyl]methyl}urea [ No CAS ]

Reference： [1]Patent: US2017/217888,2017,A1

60
[ 18515-67-8 ]
2-chloro-4-(1-[dimethyl(2-methyl-2-propanyl)silyl]oxy}-2,2,2-trifluoroethyl)-6-methylaniline [ No CAS ]

Reference： [1]Patent: US2017/217888,2017,A1

61
[ 18515-67-8 ]
[ 81290-20-2 ]
2,2,2-trifluoro-1-(3-methyl-4-nitrophenyl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃; for 1h;Cooling with ice;	To a tetrahydrofuran solution (40 mL) of <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> (2.5 g) (CAS registry number: 18515-67-8), (trifluoromethyl)trimethylsilane (6.7 mL) and tetrabutyl ammonium fluoride (1 M tetrahydrofuran solution, 0.76 mL) were added under ice-cooling. The resulting mixture was stirred at room temperature for 30 minutes. Tetrabutyl ammonium fluoride (1 M tetrahydrofuran solution, 18 mL) was added thereto under ice-cooling, and the resulting mixture was stirred at room temperature for 30 minutes. A saturated ammonium chloride aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (hexane:ethyl acetate=90:10?82:18?50:50) to obtain the title compound (2.0 g) having the following physical property values. TLC: Rf 0.50 (hexane:ethyl acetate=2:1); 1H-NMR (CDCl3): delta 2.64, 2.89, 5.06-5.14, 7.46-7.49, 7.99-8.02.

Reference： [1]Patent: US2017/217888,2017,A1 .Location in patent: Paragraph 0654-0656

62
[ 18515-67-8 ]
[ 62778-16-9 ]
(E)-2-methyl-4-(2-methylstyryl)-1-nitrobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%		To a solution of diethyl 2-methylbenzyl-phosphonate (compound 2A, 500 mg, 2.06 mmol) in THF (6 mL) was added CH3ONa (123 mg, 2.27 mmol) at 0 C., the mixture was stirred at 25 C. for 30 min, then cooled to 0 C., a solution of <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> (compound 2, 375 mg, 2.27 mmol) in THF (6 mL) was added, the mixture was stirred at 25 C. for 2 hrs. TLC (petroleum ether:ethyl acetate=1:1, Rf=0.92) showed one new point formed. The mixture was concentrated in vacuum to give yellow oil. The oil was purified by silica gel column chromatography (petroleum ether:ethyl acetate=100:0 to 50:50) to give (E)-2-methyl-4-(2-methylstyryl)-1-nitrobenzene (compound 3, 290 mg, 56% yield) as yellow solid.

Reference： [1]Patent: US2019/55218,2019,A1 .Location in patent: Paragraph 0253; 0254; 0255

63
[ 18515-67-8 ]
2-methyl-N-[2-methyl-4-[3-(o-tolyl)oxiran-2-yl]phenyl]pyrazole-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

64
[ 18515-67-8 ]
(E)-2-methyl-4-(2-methylstyryl)aniline [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

65
[ 18515-67-8 ]
(E)-1-methyl-N-(2-methyl-4-(2-methylstyryl)phenyl)-1H-pyrazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

66
[ 18515-67-8 ]
1-methyl-N-(2-methyl-4-(2-methylphenethyl)phenyl)-1H-pyrazole-5-carboxamide [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

67
[ 18515-67-8 ]
[ 1210757-61-1 ]

Reference： [1]Patent: WO2019/36407,2019,A1

68
[ 18515-67-8 ]
5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-3-(3-methyl-4-nitrophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazole [ No CAS ]

Reference： [1]Patent: WO2019/36407,2019,A1

69
[ 18515-67-8 ]
2-methyl-4-[5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]aniline [ No CAS ]

Reference： [1]Patent: WO2019/36407,2019,A1

70
[ 18515-67-8 ]
2,2,2-trifluoro-N-(2-methyl-4-[5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2019/36407,2019,A1

71
[ 18515-67-8 ]
3,3,3-trifluoro-N-(2-methyl-4-[5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl)propanamide [ No CAS ]

Reference： [1]Patent: WO2019/36407,2019,A1

72
[ 18515-67-8 ]
N-(2-methyl-4-[5-[1-methyl-3-(trifluoromethyl)-1H-pyrazol-5-yl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]phenyl)-2-(methylsulfanyl)acetamide [ No CAS ]

Reference： [1]Patent: WO2019/36407,2019,A1

73
[ 18515-67-8 ]
2,4-dimethyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrazole-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

74
[ 18515-67-8 ]
2,5-dimethyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrazole-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

75
[ 18515-67-8 ]
1-methyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrrole-2-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

76
[ 18515-67-8 ]
1-isopropyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrazole-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

77
[ 18515-67-8 ]
2-isopropyl-N-[2-methyl-4-[(E)-2-(o-tolyl)vinyl]phenyl]pyrazole-3-carboxamide [ No CAS ]

Reference： [1]Patent: US2019/55218,2019,A1

78
[ 17084-13-8 ]
[ 27318-90-7 ]
[ 18515-67-8 ]
cis-Ru(1,10-phenanthroline)₂Cl₂_*2H₂O [ No CAS ]
[Ru(phen)2MNPIP]*(PF₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The product obtained in the step (1) and the product obtained in the step (2) are dissolved in ethanol:In water (volume ratio of 2:1), the shielding gas (protective gas is inert gas, including argon, nitrogen, helium) is refluxed at 120 C for 2-3 h to obtain a deep red clear solution.Cool to room temperature, add 40 ml of water, add appropriate amount of sodium perchlorate or potassium hexafluorophosphate,A precipitate was formed, suction filtered, washed with water and diethyl ether and dried in vacuo to give a crude material.The product obtained in step (3),<strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> and ammonium acetate are dissolved in glacial acetic acid at a molar ratio of 1:1:25.Under a protective atmosphere, reflux at 120 C for 2-3 h to obtain a deep red clear solution and cool to room temperature.Pour into ice, concentrated in concentrated ammonia to a pH of about neutral,Add appropriate amount of sodium perchlorate or potassium hexafluorophosphate to produce a precipitate, suction filtration,Wash with water and diethyl ether and dry in vacuo to give a crude material. The pure product was separated by neutral alumina column chromatography, and the eluent was acetonitrile and toluene.The ratio of acetonitrile to toluene was acetonitrile: toluene = 4:1.

Reference： [1]Patent: CN109456365,2019,A .Location in patent: Paragraph 0045; 0051-0056

79
[ 17084-13-8 ]
[ 27318-90-7 ]
cis-dichlorobis(2,2'-bipyridine)ruthenium(II) dihydrate [ No CAS ]
[ 18515-67-8 ]
[Ru(2,2′-bipyridine)₂(2-(3-methyl-4-nitrophenyl)imidazo[4,5-f ]-1,10-phenanthroline)](PF₆)₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The product obtained in the step (1) and the product obtained in the step (2) are dissolved in ethanol:In the water (volume ratio of 2:1), the shielding gas (the shielding gas is an inert gas, including argon), nitrogen, helium) reflux at 120 C for 2-3 h, to obtain a deep red clear solution,Cool to room temperature, add 40 ml of water, add appropriate amount of sodium perchlorate or potassium hexafluorophosphate,The precipitate is formed, suction filtered, washed with water and diethyl ether, and dried in vacuo to give a crude product.stand-by.The product obtained in the step (3), <strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> and ammonium acetate are dissolved in glacial acetic acid at a molar ratio of 1:1:25, and refluxed under a protective atmosphere at 120 C for 2-3 hours to obtain a deep red clarification. Solution,Cool to room temperature, pour into ice, and dilute in ammonia to a pH of about neutral.Add appropriate amount of sodium perchlorate or potassium hexafluorophosphate to produce a precipitate, suction filtration,Wash with water and ether.Dry the product in vacuo to obtain a crude product. Neutral alumina column chromatography to separate pure products,The eluent is acetonitrile and toluene.The ratio of acetonitrile to toluene was acetonitrile: toluene = 4:1.

Reference： [1]Patent: CN109456365,2019,A .Location in patent: Paragraph 0031; 0037-0044

80
[ 123-75-1 ]
[ 18515-67-8 ]
[ 1435953-99-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In tetrahydrofuran;	<strong>[18515-67-8]3-methyl-4-nitrobenzaldehyde</strong> was converted into l-(3-methyl-4-nitrobenzyl)pyrroIidine by reductive amination using pyrrolidine, sodium triacetoxyborohydride, and catalytic acetic acid in tetrahydrofuran. One skilled in the art would recognize and understand how to execute this chemistry in order to produce l-(3-methyl-4-nitrobenzyl)pyrrolidine. The nitro group of l-(3- methyl-4-nitrobenzyl)pyrrolidine was reduced to the corresponding aniline, 2-methyl-4- (pyrrolidin-l-ylmethyl)aniline, using an excess of tin (II) chloride in ethyl acetate. One skilled in the art would recognize and understand how to execute this chemistry in order to produce 2- methyl-4-(pyrrolidin-l-ylmethyl)aniline. The 2-chloro-N-phenylacetamide intermediate, 2-chloro- N-(2-methyl-4-(pyrrolidin-l-ylmethyl)phenyl)acetamide, was prepared from 2-methyl-4- (pyrrolidin-l-ylmethyl)aniline using the standard procedure 1

Reference： [1]Patent: WO2019/182944,2019,A1 .Location in patent: Paragraph 0245; 0246

81
[ 18515-67-8 ]
[ 1018543-03-7 ]

Reference： [1]Patent: WO2019/182944,2019,A1

82
bis(2,2'-bipyridine)(1,10-phenanthroline-5,6-dione)ruthenium(II) bis(hexafluorophosphate) [ No CAS ]
[ 18515-67-8 ]
[Ru(2,2′-bipyridine)₂(2-(3-methyl-4-nitrophenyl)imidazo[4,5-f ]-1,10-phenanthroline)](PF₆)₂ [ No CAS ]

Reference： [1]Inorganic Chemistry,2019,vol. 58,p. 16326 - 16329

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P321
P322
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P342	If experiencing respiratory symptoms:
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 18515-67-8 ] {[proInfo.proName]}

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[ 18515-67-8 ] Synthesis Path-Upstream 1~6

[ 18515-67-8 ] Synthesis Path-Downstream 1~82

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Aryls

Aldehydes

Nitroes

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[ 18515-67-8 ]