30780-19-9|4-(4-Nitrophenyl)butan-2-one| Ambeed

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Quality Control of [ 30780-19-9 ] Purity: 95% SDS Specification

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Product Details of [ 30780-19-9 ]

CAS No. :	30780-19-9
Formula :	C₁₀H₁₁NO₃
M.W :	193.20
SMILES Code :	CC(=O)CCC1=CC=C(C=C1)[N+]([O-])=O
MDL No. :	MFCD11655141
InChI Key :	BQCIKEHCNRRAKU-UHFFFAOYSA-N
Pubchem ID :	12235672

Safety of [ 30780-19-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 30780-19-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	14
Num. arom. heavy atoms	6
Fraction Csp3	0.3
Num. rotatable bonds	4
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	54.85
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	62.89 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.6
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	2.15
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.12
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.	1.21
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	0.7
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.56

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.45
Solubility	0.693 mg/ml ; 0.00359 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.	-3.1
Solubility	0.152 mg/ml ; 0.000789 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	-2.93
Solubility	0.229 mg/ml ; 0.00118 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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.	-5.95 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	1.0
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	2.0 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)	1.61

Application In Synthesis of [ 30780-19-9 ]

* 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 [ 30780-19-9 ]

[ 30780-19-9 ] Synthesis Path-Downstream 1~41

1
[ 2550-26-7 ]
[ 30780-19-9 ]
[ 58751-62-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1905,vol. <2> 71,p. 45.

2
[ 30780-19-9 ]
[ 875854-25-4 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1908,vol. 146,p. 1410.

3
[ 2550-26-7 ]
[ 30780-19-9 ]

References: [1]Journal of the American Chemical Society,1994,vol. 116,p. 2261 - 2270.

4
[ 30780-19-9 ]
[ 13170-43-9 ]
[ 103368-94-1 ]

References: [1]Journal of Organic Chemistry,1986,vol. 51,p. 3694 - 3696.

5
2-(4-nitrobenzyl)-1-chlorocyclopropane [ No CAS ]
[ 30780-19-9 ]
2-methyl-3-(4-nitrophenyl)propanal [ No CAS ]

References: [1]Russian Journal of Organic Chemistry,1996,vol. 32,p. 817 - 825.

6
[ 636-98-6 ]
[ 598-32-3 ]
[ 30780-19-9 ]

References: [1]Journal of Chemical Research,2013,vol. 37,p. 333 - 336.
[2]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.
[3]Journal of the American Chemical Society,2012,vol. 134,p. 9890 - 9893.
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 4637 - 4640.
Angew. Chem.,2013,vol. 125,p. 4735 - 4738.

7
[ 30780-19-9 ]
[ 208838-29-3 ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 4637 - 4640.
Angew. Chem.,2013,vol. 125,p. 4735 - 4738.
[3]Journal of the American Chemical Society,2019,vol. 141,p. 12707 - 12716.

8
[ 30780-19-9 ]
C₁₀H₈⁽²⁾H₅NO₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.

9
[ 30780-19-9 ]
4-(4-nitrophenyl)-2-butanone-1,1,1,3,3-d5 [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.

11
α-<4-nitro-benzyl>-α-acetyl-acetone [ No CAS ]
[ 30780-19-9 ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1906,vol. 143,p. 753.
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1908,vol. 146,p. 1410.

12
α-<4-nitro-benzyl>-acetone-α.α'-dicarboxylic acid diethyl ester [ No CAS ]
[ 30780-19-9 ]

References: [1]Chemische Berichte,1904,vol. 37,p. 1992.

13
[ 2550-26-7 ]
[ 7697-37-2 ]
[ 30780-19-9 ]
[ 58751-62-5 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1905,vol. <2> 71,p. 45.

14
[ 30780-19-9 ]
methylmagnesium halide [ No CAS ]
[ 96784-55-3 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 115 - 118.

15
[ 30780-19-9 ]
ethylmagnesium halide [ No CAS ]
[ 96784-56-4 ]

References: [1]Tetrahedron Letters,1985,vol. 26,p. 115 - 118.

16
[ 7677-24-9 ]
[ 30780-19-9 ]
2-hydroxy-2-methyl-4-(4-nitro-phenyl)-butyronitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

17
[ 123-54-6 ]
[ 100-11-8 ]
[ 30780-19-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate; In methanol; at 75℃; for 4h;	4-Nitrobenzyl bromide(0.2 mol, 42.8 g) and 2,4-pentanedione (0.2 mol, 20 g) wereplaced a double-neck flask, and 300 mL of MeOH was added to theflask. When these were completely dissolved, 27.6 g of potassiumcarbonate was added and the mixture was refluxed for 4 h. Whenthe reaction solution temperature cooled to room temperature, thesolvent was removed under reduced pressure, and then 200 mL ofH2O was added. The mixture was extracted with EtOAc(3 x 200 mL), and then the organic layer was dried over anhydrousNa2SO4, filtered and concentrated to dryness, and purified throughsilica gel column (EA: PE 10: 1) to give 4-(4-nitrophenyl)butan-2-one as white crystals, mp 56.1-57.0 C, yield 66%; 1H NMR(300 MHz, CDCl3) δ 8.08 (d, J = 8.7 Hz, 2H, Ar-H), 7.32 (d, J=8.7 Hz,2H, Ar-H),2.96 (t, J = 7.3 Hz, 2H, benzylic CH2), 2.79 (t, J = 7.2 Hz, 2H,-CO-CH2), 2.13 (s, 3H, -CO-CH3); 13C NMR (75 MHz, CDCl3) δ 206.83(carbonyl), 149.09, 146.45, 129.31, 123.71, 44.14 (benzylic CH2),30.06 (-CO-CH2), 29.33 (-CO-CH3); ESI-HRMS m/z: 194.0814[M+H]+, calcd for C10H12NO3 194.0812.

References: [1]European Journal of Medicinal Chemistry,2017,vol. 127,p. 187 - 199.
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

18
[ 598-32-3 ]
p-nitrobenzenediazonium o-benzenedisulfonimide [ No CAS ]
[ 30780-19-9 ]
[ 63099-53-6 ]
[ 86983-89-3 ]

References: [1]Synthesis,2006,p. 3443 - 3452.

19
[ 30780-19-9 ]
4-(4-amino-phenyl)-2-hydroxy-2-methyl-butyryl chloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

20
[ 30780-19-9 ]
[ 911297-06-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

21
[ 30780-19-9 ]
[ 911297-05-7 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

22
[ 30780-19-9 ]
[ 911297-07-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

23
[ 30780-19-9 ]
2-hydroxy-4-(4-isothiocyanatophenyl)-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)butanamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 6525 - 6538.

24
[ 30780-19-9 ]
[ 208838-30-6 ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.

25
[ 30780-19-9 ]
2-bromo-4-(4-nitrophenyl)butane-1,1,1,3,3-d5 [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.

26
[ 30780-19-9 ]
O-methanesulfonyl-4-(4-nitrophenyl)-2-butanol [ No CAS ]

References: [1]Journal of the American Chemical Society,1998,vol. 120,p. 5160 - 5167.

27
[ 30780-19-9 ]
4-(4-amino-phenyl)-butan-2-one semicarbazone [ No CAS ]

References: [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1908,vol. 146,p. 1410.

28
[ 30780-19-9 ]
[ 133691-35-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; sodium acetate; pyridinium hydrobromide perbromide; thiourea; In methanol; ethanol; chloroform; water; acetic acid;	EXAMPLE 1 A solution of 1-acetyl-2-(4-nitrophenyl)ethane (9.6 g) and pyridinium bromide perbromide (18 g) in acetic acid and 35% hydrogen bromide in acetic acid (21 ml) was stirred at room temperature for 5 hours. The reaction mixture was washed with isopropyl ether and decanted. To the residue was added the thiourea (6 g), sodium acetate (8 g) and ethanol (150 ml). The mixture was heated at 50 C. for 2 hours with stirring. The reaction mixture was concentrated in vacuo and to the residue was added water and then the mixture was adjusted to pH 8. The solution was extracted with ethyl acetate and washed with 10% aqueous hydrochloric acid and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was subjected to column chromatography on silica gel (silica gel 60, 70-230 mesh; Merck: 300 g) and eluted with a mixture of chloroform and methanol (10:1). The fractions containing the objective compound were combined and concentrated under reduced pressure to give 2-amino-4-methyl-5-(4-nitrobenzyl)thiazole (2.0 g, yield: 16.2%). IR (Nujol): 3200, 3250, 3350, 1630, 1605, 1515, 1350 cm-1 NMR (DMSO-d6, 90 MHZ, ppm): 2.20 (3H, s), 4.10 (2H, s), 7.50 (2H, d, J=9 Hz), 8.16 (2H, d, J=9 Hz), 8.85 (2H, s) Mass: M+1 250, M 249, m/e 234, 204, 190, 127

References: [1]Patent: US5256675,1993,A .

29
[ 30780-19-9 ]
[ 104-15-4 ]
[ 7568-93-6 ]
[ 93788-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; diethyl ether; toluene;	EXAMPLE 9 1-Phenyl-2-[1-methyl-3-(4-nitrophenyl)propylamino]ethanol A solution of 5.0 g. (25.9 mM) of 2-amino-1-phenylethanol and 3.55 g. (25.9 mM) of methyl 2-(4-nitrophenyl)ethyl ketone in 60 ml. of toluene containing 10 mg. of para-toluenesulfonic acid was heated at reflux for six hours in a flask equipped with a Dean-Stark trap. The water that formed during the reaction was removed via the trap, and then the reaction mixture was cooled to room temperature and concentrated to dryness by evaporation of the solvent under reduced pressure. The solid product that remained was dissolved in 50 ml. of tetrahydrofuran and the solution was heated to reflux. A solution of 13.5 ml. of 2N borane-methyl sulfide complex in tetrahydrofuran was then added dropwise to the reaction mixture, and the mixture was refluxed for an additional ninety minutes. After cooling the reaction mixture to room temperature, it was diluted by addition of diethyl ether saturated with hydrogen chloride. The precipitate that formed was collected by filtration and crystallized from ethanol and diethyl ether to give 3.29 g. of 1-phenyl- 2-[1-methyl-3-(4-nitrophenyl)propylamino]ethanol hydrochloride. M.P. 203-213 C. Analysis calc. for C18 H23 ClN2 O3: Theory: C, 61.62; H, 6.61; N, 7.98; Cl, 10.11. Found: C, 61.76; H, 6.62; N, 7.76; Cl, 10.13.

References: [1]Patent: US4690951,1987,A .

30
4-(p-nitrophenyl)-3-butene-2-one [ No CAS ]
[ 30780-19-9 ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 3528 - 3532.
[2]Angewandte Chemie - International Edition,2010,vol. 49,p. 4976 - 4980.
[3]ACS Catalysis,2018,vol. 8,p. 2413 - 2419.

31
[ 30780-19-9 ]
[ 107-21-1 ]
[ 1272975-51-5 ]

Yield	Reaction Conditions	Operation in experiment
	With camphor-10-sulfonic acid; In toluene;Inert atmosphere; Reflux;	General procedure: A 500 mL flask equipped with a Dean-Stark apparatus was charged with ketone (0.1 mol), ethylene glycol (31 g, 0.5 mol) or catechol (16.5 g, 0.15 mol), camphor-10-sulfonic acid (1 g, 4.3 mmol), and toluene (200 mL). The mixture was refluxing, and completion of the reaction was followed by TLC. Then, for the preparation of ethylene ketals, the solution was washed with saturated aqueous solution of NaHCO3, and dried over MgSO4. For the preparation of dioxoles, the solution was stirred for 2 h with anhydrous K2CO3 (15 g) and then filtered. The solvent was evaporated in vacuo, and the residue was flash chromatographed on silica gel.

References: [1]Tetrahedron,2011,vol. 67,p. 1448 - 1455.

32
(E)-4-(4-nitrophenyl)-3-buten-2-one [ No CAS ]
[ 30780-19-9 ]

References: [1]Chemistry - An Asian Journal,2012,vol. 7,p. 351 - 359.

33
[ 555-16-8 ]
[ 30780-19-9 ]

References: [1]Chemistry - An Asian Journal,2012,vol. 7,p. 351 - 359.

34
[ 30780-19-9 ]
[ 1381772-57-1 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 9890 - 9893.

35
[ 30780-19-9 ]
[ 1381772-77-5 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 9890 - 9893.

36
[ 30780-19-9 ]
[ 1073-69-4 ]
[ 1381772-23-1 ]
[ 1381772-19-5 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 9890 - 9893.

37
[ 30780-19-9 ]
C₂₅H₂₄N₂O₂ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 4637 - 4640.
Angew. Chem.,2013,vol. 125,p. 4735 - 4738.

38
[ 100-11-8 ]
[ 30780-19-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2553 - 2562.
[2]Patent: WO2015/51362,2015,A1 .
[3]Patent: CN107759481,2018,A .

39
[ 61713-40-4 ]
[ 30780-19-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrogenchloride; acetic acid; In water; for 24h;Reflux;	Compound 6 (10 g, 37.7 mmol) was dissolved in the mixture ofacetic acid (85 mL) and concd HCl solution (30 mL), and the resultingsolution was refluxed for 24 h after which the reaction mixturewas allowed to room temperature and concentrated to dryness invacuo. The residue was treated with H2O (100 ml) and extractedwith ethyl acetate (2 100 mL). The combined organic layers weredried over MgSO4, filtered, and concentrated in vacuo to providepure 7 (7.3 g, 100%). 1H NMR (CDCl3, 300 MHz) d 2.09 (s, 3H),2.77 (t, 2H, J = 9 Hz), 2.92 (t, 2H, J = 9 Hz), 7.29 (d, 2H, J = 9 Hz),8.01 (d, 2H, J = 9 Hz); 13C NMR (CDCl3, 75 MHz) d 29.3 (t), 30.1(q), 44.2 (t), 123.7 (d), 129.3 (d), 146.5 (s), 149.0 (s), 206.8 (s).The data of 1H and 13C NMR data were essentially identical to thoseof 7 as previously reported
100%	With hydrogenchloride; acetic acid; In water; for 24h;Reflux;	Compound 6 (10 g, 37.7 mmol) was dissolved in the mixture of acetic acid (85 mL) and conc. HCI (30 mL), and the resulting solution was refluxed for 24 h after which the reaction mixture was allowed to room temperature and concentrated to dryness in vacuo. The residue was treated with H20 (100 ml) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to provide pure 7 (7.3g. 100%). ‘Fl NMR (CDCI3, 300 MHz) 6 2.95 (s, 3H), 2.77 (t, 2H, J= 7.5 Hz), 2.92 (t, 211, J= 7.5 Hz), 7.28 (d, 2H, J= 8.8 Hz), 8.01 (d, 211, J8.8 Hz); ‘3C NMR (CDCI3, 300 MHz) 329.27 (t), 29.95 (q), 123.58 (d), 129.27 (d), 146.32 (s),149.15 (s), 206.7(s). The data of ‘H and ‘3C NMR data were essentially identical to those of 7 as previously reported.
93%	With hydrogenchloride; acetic acid; In water; for 18h;Reflux;	The product obtained in step (1) above (13.3 g, 50 mmol), acetic acid (100 mL) and concentrated hydrochloric acid (50 mL) were mixed well and heated under reflux for 18 h until thin layer chromatography showed that the reaction had been completed. Acetic acid was removed as much as possible. The remaining residue was dissolved in water (200 mL), extracted with ethyl acetate (2 x 200 mL), and dried over anhydrous magnesium sulfate. The solvent was spun off to give 9.0 g (yield: 93%) of a pale yellow oil. The 1H NMR data is in complete agreement with the literature.

	With acetic acid; In water; at 110℃; for 24h;	The concentrated solution obtained by the above reaction was added to a 5M acetic acid solution, and the oil bath was heated to 110C.Keep the temperature for 24 hours, during which time bubbles appear. After the reaction is completed, the reaction is stopped and the reaction is cooled to room temperature.Saturated Na2CO3 solution was added to remove excess acetic acid and the pH was adjusted to alkaline (pH>10).Finally, ethyl acetate was added to extract in an atmospheric separatory funnel three times, and the organic phase was collected in an Erlenmeyer flask.Dry over anhydrous magnesium sulfate and concentrate using a rotary evaporator to give a crude sample.After purification by column chromatography (petroleum ether:ethyl acetate=10:1, volume ratio), the compound of Formula 2 was obtained.The total output of the above two-step reaction is 50%.
	With acetic acid; at 110℃; for 24h;	The above reaction of the concentrate is added to the 5 M in acetic acid solution, the oil bath heated to 110 C after, maintain the temperature for 24 hours, in the course of the air bubble out. After the reaction, stopping the reaction, the reaction is cooled to room temperature, adding saturated Na2CO3 solution, to remove the surplus acetic acid, adjusting pH value to alkaline (pH 10>). Finally adding ethyl acetate in a separatory funnel extraction three times normal, for collecting the organic phase in the flask, adding anhydrous magnesium sulfate drying, using a rotary evaporator after concentrating, to obtain crude sample, after column chromatography (petroleum ether: ethyl acetate=10:1, volume ratio) purification of formula 2 as shown in, the above two-step reaction of the total output is 50%.

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2553 - 2562.
[2]Patent: WO2015/51362,2015,A1 .Location in patent: Page/Page column 37.
[3]Patent: CN107963976,2018,A .Location in patent: Paragraph 0105; 0108.
[4]Patent: CN107759481,2018,A .Location in patent: Paragraph 0040; 0043; 0044.
[5]Patent: CN109748803,2019,A .Location in patent: Paragraph 0023; 0029-0031.

40
[ 30780-19-9 ]
[ 1598386-21-0 ]

Yield	Reaction Conditions	Operation in experiment
18%	With bromine; In methanol; at 7 - 9℃; for 35h;	2.8 1-Bromo-<strong>[30780-19-9]4-(4-nitrophenyl)butan-2-one</strong> (8) To a solution of 7 (5.0 g, 25.88 mmol) in anhydrous methanol (10 mL) was added dropwise bromine (4.14 mg, 25.88 mmol) in anhydrous methanol (10 mL) at 7-9 C over 1 h. The mixture was stirred for 34 h at the same temperature. DI water (30 mL) was added to the mixture which was warmed to room temperature and continuously stirred for 12 h. The reaction mixture was extracted with CH2Cl2 (2 * 30 mL). The combined organic layers were dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified via column chromatography on silica gel (60-220 mesh) and eluted with 10% ethyl acetate in hexanes to afford 8 (1.26 g, 18%) as a solid. 1H NMR (CDCl3, 300 MHz) δ 3.05 (s, 4H), 3.87 (s, 2H), 7.35 (d, 2H, J = 7.8 Hz), 8.12 (d, 2H, J = 8.1 Hz); 13C NMR (CDCl3, 75 MHz) δ 29.4 (t), 33.9 (t), 40.4 (t), 123.8 (d), 129.3 (d), 146.6 (s), 148.2 (s), 200.4 (s). HRMS (positive ion ESI) Calcd for C10H11BrNO3 [M+H]+ m/z 271.9917. Found: [M+H]+ m/z 271.9924.
18%	With bromine; In methanol; at 7 - 9℃; for 34h;	To a solution of 7 (5.0 g, 25.88 mmol) in anhydrous methanol (10 mL) was added dropwise bromine (4.14 mg, 25.88 mmol) in anhydrous methanol (10 mL) at 7-9C over I h. The mixture was stirred for 34 h in same temperature. DI water (30 mL) was added to the mixture which was warmed to room temperature and continuously stirred for 12 h. The reaction mixture was extracted with CH2CI2 (2 x 30 mL). The combined organic layers were dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified via column chromatography on silica gel (60-220 mesh) and eluted with 10% ethyl acetate in hexanes to afford 8 (1.26 g, 18.0%) as a solid. ‘H NMR (CDCI3, 300 MHz) 6 3.04 (s, 411), 3.87 (s, 2H), 7.35 (d, 2H, J 8.8 Hz), 8.12 (d, 2H, J 8.8 Hz); 13C NMR (CDCI3, 300 MHz) 629.30(t), 33.88 (t), 40.32 (t), 123.8 (d), 129.32 (d), 146.61 (s), 148.23 (s), 200.43 (s). HRMS (positive ion ESI) Calcd for C10H1 1BrNO3 [M + HJ m/z 271.9917. Found:[M + H] rn/z 271.9924.

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2553 - 2562.
[2]Patent: WO2015/51362,2015,A1 .Location in patent: Page/Page column 37; 38.

41
[ 30780-19-9 ]
[ 1598386-22-1 ]

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 2553 - 2562.
[2]Patent: WO2015/51362,2015,A1 .

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• Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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