[ CAS No. 15893-42-2 ] {[proInfo.proName]}

Name: 15893-42-2|3-(4-Methoxyphenyl)propanoyl chloride|97%
Brand: Ambeed
SKU: A286870
Rating: 92 (26 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 15893-42-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 15893-42-2 ]

CAS No. :	15893-42-2	MDL No. :	MFCD02258671
Formula :	C₁₀H₁₁ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FQVJPHCAWYRYCK-UHFFFAOYSA-N
M.W :	198.65	Pubchem ID :	10932441
Synonyms :

Safety of [ 15893-42-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501	UN#:	1760
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 15893-42-2 ]

* 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 [ 15893-42-2 ]
Downstream synthetic route of [ 15893-42-2 ]

[ 15893-42-2 ] Synthesis Path-Upstream 1~2

1
[ 15893-42-2 ]
[ 13623-25-1 ]

Reference： [1] Journal of Organic Chemistry, 1984, vol. 49, # 14, p. 2517 - 2520
[2] Journal of Organic Chemistry, 1970, vol. 35, p. 647 - 651
[3] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155

2
[ 15893-42-2 ]
[ 62803-47-8 ]

Reference： [1] Molecular Crystals and Liquid Crystals, 2011, vol. 545, p. 149 - 155

[ 15893-42-2 ] Synthesis Path-Downstream 1~88

1
[ 39067-45-3 ]
[ 15893-42-2 ]
3-(4-methoxy-phenyl)-propionic acid-(3-diethylamino-2,2-dimethyl-propyl ester) [ No CAS ]

Reference： [1]Doklady Akademii Nauk Armyanskoi SSR,1955,vol. 21,p. 223,225
Chem.Abstr.,1956,p. 11281

2
[ 1929-29-9 ]
[ 15893-42-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With phosgene; In water monomer; at 20℃; for 4h;	General procedure: Cinnamoyl chlorides - Derivatives of cinnamic acid were stirred with oxalyl chloride (5 ml g-1) for up to 4 h. The stirring time differed depending on the dissolution rate of the starting cinnamic acid derivative. For derivatives with 4-NO2 or 4-N(CH3)2 substituents, a drop of dry N,N-DMF was added to catalyze the reaction. The excess reagent was evaporated under reduced pressure. The hydroxy groups in the hydroxycinnamic acid derivatives were acetylated prior to reaction with oxalyl chloride by stirring the derivative (0.0244 mol) in acetic anhydride (5 ml g-1) and pyridine (0.5 ml) at room temperature (rt, ~20 C) overnight. Cold water (~50 ml) was added to the mixture and stirred for further 5-10 min with cooling in an ice-water bath, and the resulting precipitate of acetoxycinnamic acid was obtained by vacuum filtration, washed with cold water and dried.Methyl N-cinnamoylanthranilates - The cinnamoyl chloride (0.014 mol) was added to a solution of excess methyl anthranilate (0.017 mol) in dry pyridine (10 ml g-1), and the mixture was stirred for an hour at rt. Cold water (250 ml) was added to the reaction mixture and the resulting precipitate was filtered and washed with cold water until free of pyridine, and was recrystallized from hot ethanol. In contrast, methyl N-hydrocinnamoylanthranilate derivatives, with a low melting point, were extracted in diethyl ether (2 × 70 ml), washed with cold water (2 × 50 ml) and the solvent evaporated under reduced pressure.N-Cinnamoylanthranilic acids - The methyl N-cinnamoylanthranilate (0.010 mol) was stirred in a mixture of THF (100 ml) and methanol (20 ml), and LiOH.H2O (0.050 mol) [LiOH dissolved in water 0.2 g per 10 ml] was added to the reaction mixture and stirred at rt overnight. The excess reagent and solvents were evaporated under reduced pressure. The crude product was dissolved in water (~350 ml) and acidified slowly to pH 4 using dilute HCl (1 M) with stirring. The precipitate was obtained by vacuumfiltration, washed with water and dried, and was recrystallized from hot aqueous ethanol (water-ethanol, 1:4). In the case of N-hydroxycinnamoylanthranilate derivatives, water was added to the resulting solution to aid crystallization.α-Methylcinnamic acid - To a mixture of benzaldehyde (5 ml, 0.0492 mol) and propionic anhydride61 (10 ml, 0.0780 mol), anhydrous sodium acetate (2.5 g) was added and heated under reflux for 4 h. Once the mixture has cooled down to rt, cold water (50 ml) was added and alkalized with saturated aqueous sodium carbonate (85 ml). The resulting solid suspension was heated up to dissolve completely, and the unreacted benzaldehyde was extracted in DCM (2 × 25 ml) and the aqueous layer was acidified with concentrated HCl (12 M) with cooling. The pale yellowish white crystals (yield 2.098 g, 26 %) of α-methylcinnamic acid was obtained by vacuum filtration, washed with little cold water (~10 ml) and dried.
	With thionyl chloride; In toluene;	a) Preparation of 3-(4-methoxyphenyl)propionyl Chloride To a suspension of 3-(4-methoxyphenyl)propionic acid (10 g) in 150 ml of toluene are added 8 ml of thionyl chloride and the mixture is heated to 65 C. for 4 hours. The solvent is evaporated off under reduced pressure and the residue is redissolved in toluene and concentrated to dryness. Such steo is repeated twice. 11 g of the product are obtained as a yellow oil.
	With thionyl chloride; In dichloromethane; for 3h;Reflux;	General procedure: A solution of 3-(4-fluorophenyl)propionic acid (300 mg, 1.8 mmol) in dry CH2Cl2 (20 mL) was treated with thionyl chloride (2.2 mL, 30.2 mmol). The reaction mixture was refluxed for 3 h and the solvent was then removed until dryness. A translucent oil, corresponding to 3-(4-fluorophenyl)propanoyl chloride, was obtained and used directly in the next reaction under the same conditions described in the general procedure.

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 2h;	Step 1 Oxalyl chloride (5 eq) was added to a solution of 4-methoxyphenyl)propionic acid (1 eq) in CH2CI2 (0.1 M), and then a catalytic amount of DMF was added to the reaction mixture to initiate the reaction and bubbling occurred. The reaction was complete in 2 hours, and the solution was dried with N2 for one hour to give the acid chloride, which was used immediately in the next step.
	With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 75℃; for 3h;	A solution of p-methoxyphenylpropionic acid (12a, 2.99 mmol), SOCl2 (2 mL) and DMF (2 drops) was added to toluene (20 mL) and stirred at 75C for 3 h. The reaction was terminated and the solution was concentrated to dryness under reduced pressure to give p-methoxyphenylpropionyl chloride (13a). (6,2.61 mmol), pyridine (1 mL) in CH2Cl2 (10 mL) was added dropwise with stirring Oxyphenylpropionyl chloride (13a). After completion of the dropwise addition, the reaction was refluxed for 2 h. The reaction was completed, cooled to room temperature, poured into dilute hydrochloric acid, stirred. Extracted with dichloromethane, and washed with saturated brine. The solvent was concentrated to dryness under reduced pressure to give crude product. Column chromatography (petroleum ether / ethyl acetate: 15/1, V / V) gave a white solid in 66.8%
	With phosphorus(V) chloride; In dichloromethane;Reflux;	General procedure: To a solution of phosphorus pentachloride (0.126 g, 0.610 mmol) in dichloromethane (11 mL), phenoxyacetic acid (0.092 g, 0.610 mmol) was added with stirring and the mixture refluxed for 30-40 minutes. After cooling, 4-methyl-1,2,5-oxadiazol-3-amine (0.060 g, 0.610 mmol) was added and the solution refluxed for 2-2.5 hours. The solvent was removed under reduced pressure and the residue quenched with water (50 mL). The solid was collected by vacuum filtration and washed with saturated sodium bicarbonate solution followed by water to afford compound 19 (0.103 g, 73%)
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 5h;	General procedure: An oven-dried flask was charged with aliphatic carboxylic acid (1.00 equiv) and CH2Cl2 (0.50 M). Three drops of N,N-dimethylformamide (DMF) and oxalyl chloride (1.20 equiv, 1.00 M) in DCM were added dropwise. The reaction mixture was stirred vigorously at room temperature for 5 h and then evaporated DCM and redundant oxalyl chloride under the vacuum. The crude acid chloride was used for the next reaction without any further purification
	With oxalyl dichloride; N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere;	General procedure: Oxalyl chloride (2equiv) was added at room temperature into asolutioncarboxylic acids(1equiv) in anhydrous dichloromethane. Added one drop ofN,N-dimethylformamide and reacted under nitrogen atmosphere for 1h. The solvent was removed under vacuum, yielding a crude product that were stored in a nitrogen atmosphere for subsequent use without further purified.

Reference： [1]European Journal of Medicinal Chemistry,2005,vol. 40,p. 764 - 771
[2]Journal of the American Chemical Society,2015,vol. 137,p. 7656 - 7659
[3]European Journal of Medicinal Chemistry,2019,vol. 170,p. 141 - 156
[4]Organic Letters,2020,vol. 22,p. 2902 - 2907
[5]Journal of the Chemical Society,1909,vol. 95,p. 1722
[6]Journal of Medicinal Chemistry,1981,vol. 24,p. 451 - 454
[7]Journal of Medicinal Chemistry,1986,vol. 29,p. 2465 - 2472
[8]Phytochemistry,1981,vol. 20,p. 1097 - 1104
[9]Journal of the Chemical Society. Perkin transactions I,1982,p. 2407 - 2412
[10]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 519 - 522
[11]Synlett,2004,p. 477 - 480
[12]Pharmazie,2004,vol. 59,p. 744 - 752
[13]Journal of Medicinal Chemistry,2006,vol. 49,p. 1494 - 1498
[14]Journal of Organic Chemistry,2000,vol. 65,p. 4179 - 4184
[15]Journal of Organic Chemistry,2001,vol. 66,p. 7166 - 7177
[16]Patent: US6110924,2000,A
[17]Organic Letters,2008,vol. 10,p. 2601 - 2604
[18]Patent: US6335332,2002,B1 .Location in patent: Page column 11
[19]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3561 - 3571
[20]Journal of Medicinal Chemistry,2009,vol. 52,p. 3366 - 3376
[21]Organic Letters,2010,vol. 12,p. 3990 - 3993
[22]Molecular Crystals and Liquid Crystals,2011,vol. 545,p. 149 - 155
[23]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445
[24]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3221 - 3230
[25]Synlett,2012,vol. 23,p. 2389 - 2392
[26]Organic Letters,2014,vol. 16,p. 1268 - 1268
[27]Patent: WO2015/35051,2015,A1 .Location in patent: Page/Page column 232
[28]Advanced Synthesis and Catalysis,2016,vol. 358,p. 887 - 893
[29]Angewandte Chemie - International Edition,2016,vol. 55,p. 6988 - 6991
    Angew. Chem.,2016,vol. 128,p. 7102 - 7105,4
[30]Journal of the American Chemical Society,2017,vol. 139,p. 2200 - 2203
[31]Patent: CN106146450,2016,A .Location in patent: Paragraph 0204; 0205; 0206
[32]Angewandte Chemie - International Edition,2017,vol. 56,p. 12307 - 12311
    Angew. Chem.,2017,vol. 129,p. 12475 - 12479,5
[33]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 6267 - 6272
[34]Journal of Medicinal Chemistry,2018,vol. 61,p. 5199 - 5221
[35]Organic Letters,2019,vol. 21,p. 3625 - 3630
[36]Tetrahedron,2019,vol. 75,p. 4186 - 4191
[37]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 2327 - 2331
[38]Journal of the American Chemical Society,2019,vol. 141,p. 16362 - 16373
[39]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175
    Angew. Chem.,2021,vol. 133,p. 173 - 177,5
[40]Journal of Medicinal Chemistry,2021,vol. 64,p. 1844 - 1855
[41]Organic Letters,2021,vol. 23,p. 3310 - 3314
[42]Biomolecules,2022,vol. 12
[43]Bioorganic and Medicinal Chemistry Letters,2022,vol. 64

3
[ 15893-42-2 ]
[ 20401-88-1 ]

Yield	Reaction Conditions	Operation in experiment
44%	With iron(II) oxide; tris(2,4,6-trimethoxyphenyl)phosphine; phenylsilane; In toluene; at 60℃; for 2h;Inert atmosphere; Schlenk technique;	General procedure: A typical procedure for the iron oxide catalyzed reduction of 3-phenylpropionyl chloride (1a) with H3SiPh (Table1 , entry 1): iron oxide (3.6mg, 0.050mmol) and TMPP (6.7mg, 0.013mmol) were added to a 10mL Schlenk flask with a magnetic stir bar. The flask was evacuated and backfilled with argon three times. Then, H3SiPh (34μL, 0.28mmol) was added to the flask and the reaction mixture was stirred at 60C for 20h under an argon atmosphere. Then, toluene (0.50mL) was added to the flask and the resultant solution was stirred at room temperature for 5min before 1a (37μL, 0.25mmol) was loaded. Further, the reaction mixture was stirred at 60C for 20h under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (5.0mL) and tetradecane (50μL, 0.19mmol) as an internal standard was added. The yield of 3-phenylpropanal (2a; 57%) was analyzed by gas chromatography. 2a was isolated by silica gel column chromatography (hexane: EtOAc=13: 1). Pale yellow oil (16.8mg) was obtained in 50% yield.

Reference： [1]Synlett,2012,vol. 23,p. 2389 - 2392
[2]Catalysis Communications,2014,vol. 50,p. 25 - 28
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1959,vol. 79,p. 1069,1072
Chem.Abstr.,1960,p. 4561
[4]Synlett,2006,p. 869 - 872
[5]Synlett,2004,p. 477 - 480

4
[ 15893-42-2 ]
[ 25413-27-8 ]

Yield	Reaction Conditions	Operation in experiment
33.4 mg	With ammonium hydroxide; In dichloromethane; at 0 - 20℃; for 0.333333h;	Step 2 Ammonium hydroxide (0.13 M) was added to a solution of acid chloride (1 eq) in CH2C12 (0.2 M) at 0 C. The reaction mixture stirred for 20 minutes at rt. The reaction mixture was extracted into CH2C12 and the organic layer was dried with Na2S04 and concentrated to give the amide as a white solid in 35% yield over 2 steps, 33.4 mg. 1H NMR (500 MHz, DMSO-d6) δ 7.27 (s, 1H), 7.12 - 7.08 (m, 2H), 6.84 - 6.79 (m, 2H), 6.78 - 6.73 (m, 1H), 3.70 (s, 3H), 2.71 (t, J= 7.7 Hz, 2H), 2.29 (t, J= 7.8 Hz, 2H). ESI-MS (m z): 180.0 [M+H]+.

Reference： [1]Journal of the Chemical Society,1930,p. 21,23
[2]Journal of the Chemical Society,1909,vol. 95,p. 1722
[3]Journal of Medicinal Chemistry,2009,vol. 52,p. 3366 - 3376
[4]Patent: WO2015/35051,2015,A1 .Location in patent: Page/Page column 232
[5]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175
Angew. Chem.,2021,vol. 133,p. 173 - 177,5

5
[ 15893-42-2 ]
[ 20387-29-5 ]

Reference： [1]Journal of the American Chemical Society,1968,vol. 90,p. 4038 - 4051

6
[ 67-52-7 ]
[ 15893-42-2 ]
[ 113379-21-8 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210
[2]Patent: US6335332,2002,B1 .Location in patent: Page column 11

7
[ 1143-38-0 ]
[ 15893-42-2 ]
[ 151562-49-1 ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 4099 - 4107

8
[ 15893-42-2 ]
[ 96495-22-6 ]
[ 144181-33-9 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4408 - 4414

9
[ 15893-42-2 ]
[ 593-56-6 ]
[ 103831-07-8 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 3394 - 3403
[2]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175
Angew. Chem.,2021,vol. 133,p. 173 - 177,5

10
[ 15893-42-2 ]
[ 142260-67-1 ]
[ 147862-36-0 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3156 - 3169

11
[ 15893-42-2 ]
[ 13623-25-1 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 2517 - 2520
[2]Journal of Organic Chemistry,1970,vol. 35,p. 647 - 651
[3]Molecular Crystals and Liquid Crystals,2011,vol. 545,p. 149 - 155
[4]Journal of Medicinal Chemistry,2021,vol. 64,p. 1844 - 1855

12
[ 15893-42-2 ]
[ 134-20-3 ]
[ 83988-43-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In water; at 20℃; for 1h;	General procedure: Cinnamoyl chlorides - Derivatives of cinnamic acid were stirred with oxalyl chloride (5 ml g-1) for up to 4 h. The stirring time differed depending on the dissolution rate of the starting cinnamic acid derivative. For derivatives with 4-NO2 or 4-N(CH3)2 substituents, a drop of dry N,N-DMF was added to catalyze the reaction. The excess reagent was evaporated under reduced pressure. The hydroxy groups in the hydroxycinnamic acid derivatives were acetylated prior to reaction with oxalyl chloride by stirring the derivative (0.0244 mol) in acetic anhydride (5 ml g-1) and pyridine (0.5 ml) at room temperature (rt, ~20 C) overnight. Cold water (~50 ml) was added to the mixture and stirred for further 5-10 min with cooling in an ice-water bath, and the resulting precipitate of acetoxycinnamic acid was obtained by vacuum filtration, washed with cold water and dried.Methyl N-cinnamoylanthranilates - The cinnamoyl chloride (0.014 mol) was added to a solution of excess methyl anthranilate (0.017 mol) in dry pyridine (10 ml g-1), and the mixture was stirred for an hour at rt. Cold water (250 ml) was added to the reaction mixture and the resulting precipitate was filtered and washed with cold water until free of pyridine, and was recrystallized from hot ethanol. In contrast, methyl N-hydrocinnamoylanthranilate derivatives, with a low melting point, were extracted in diethyl ether (2 × 70 ml), washed with cold water (2 × 50 ml) and the solvent evaporated under reduced pressure.N-Cinnamoylanthranilic acids - The methyl N-cinnamoylanthranilate (0.010 mol) was stirred in a mixture of THF (100 ml) and methanol (20 ml), and LiOH.H2O (0.050 mol) [LiOH dissolved in water 0.2 g per 10 ml] was added to the reaction mixture and stirred at rt overnight. The excess reagent and solvents were evaporated under reduced pressure. The crude product was dissolved in water (~350 ml) and acidified slowly to pH 4 using dilute HCl (1 M) with stirring. The precipitate was obtained by vacuumfiltration, washed with water and dried, and was recrystallized from hot aqueous ethanol (water-ethanol, 1:4). In the case of N-hydroxycinnamoylanthranilate derivatives, water was added to the resulting solution to aid crystallization.α-Methylcinnamic acid - To a mixture of benzaldehyde (5 ml, 0.0492 mol) and propionic anhydride61 (10 ml, 0.0780 mol), anhydrous sodium acetate (2.5 g) was added and heated under reflux for 4 h. Once the mixture has cooled down to rt, cold water (50 ml) was added and alkalized with saturated aqueous sodium carbonate (85 ml). The resulting solid suspension was heated up to dissolve completely, and the unreacted benzaldehyde was extracted in DCM (2 × 25 ml) and the aqueous layer was acidified with concentrated HCl (12 M) with cooling. The pale yellowish white crystals (yield 2.098 g, 26 %) of α-methylcinnamic acid was obtained by vacuum filtration, washed with little cold water (~10 ml) and dried.

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1982,p. 2407 - 2412
[2]European Journal of Medicinal Chemistry,2019,vol. 170,p. 141 - 156

13
[ 31926-62-2 ]
[ 15893-42-2 ]
3-(4-methoxy-phenyl)-propionic acid naphtho[2,3-b]thiophen-4-yl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 7816 - 7825

14
[ 943-89-5 ]
[ 15893-42-2 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1494 - 1498

15
[ 15893-42-2 ]
2-{2,5-dimethoxy-4-[3-(4-methoxy-phenyl)-propyl]-phenyl}-1-methyl-ethylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3074 - 3084

16
[ 15893-42-2 ]
[ 1026133-26-5 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3074 - 3084

17
[ 15893-42-2 ]
[ 113378-98-6 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210

18
[ 15893-42-2 ]
[ 113379-02-5 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210

19
[ 15893-42-2 ]
[ 113379-22-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210

20
[ 15893-42-2 ]
2,4-Diaza-dispiro[5.0.5.3]pentadeca-8,11-diene-1,3,5,10-tetraone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210

21
[ 15893-42-2 ]
[ 113379-27-4 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210

22
[ 15893-42-2 ]
C₁₈H₁₄O₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 2210

23
[ 15893-42-2 ]
[ 103831-04-5 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 3394 - 3403
[2]Angewandte Chemie - International Edition,2021,vol. 60,p. 171 - 175
Angew. Chem.,2021,vol. 133,p. 173 - 177,5

24
[ 15893-42-2 ]
[ 121670-33-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrazine; In ethanol; for 16h;Heating / reflux;	[2-(4-Methoxy-phenyl)-ethyl]-hydrazine l0409] 1- (2-CHLORO-ETHYL)-4-METHOXY-BENZENE (1 ML, 6.6 mmol) and hydrazine monohydrate (0.96 ML, 19. 6 mmol) were dissolved in ethanol. It was REFLUXED for 16 h, the solvent was removed and the solid was washed with ethyl acetate. The title compound was obtained in 87% yield as a white solid.

Reference： [1]Patent: WO2005/5378,2005,A2 .Location in patent: Page/Page column 86

25
3-amino-1-(3-chlorobenzyl)-6-(3,5-difluorophenyl)indole-2-carboxylic acid ethyl ester [ No CAS ]
[ 15893-42-2 ]
1-(3-chlorobenzyl)-6-(3,5-difluorophenyl)-3-[3-(4-methoxyphenyl)-propionylamino]indole-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dmap; triethylamine; In acetonitrile; at 20℃;	(b) 1- (3-CBLOROBENZYI)-6- (3, 5-DIFLUOROPHENYL)-3-F3- (4-METHOXVPHENVL)- PROPIONYLAMINOLINDOLE-2-CARBOXYLIC acid ethyl ester DMAP (22.3 mg, 0.18 mmol) and Et3N (154 JUS, 1. 1 mmol) were added at room temperature to a stirred mixture of 3-AMINO-1- (3-CHLOROBENZYL)-6- (3,5-difluorophenyl) INDOLE-2-CARBOXYLIC acid ethyl ester (150 mg, 0.37 mmol), 3- (4-METHOXYPHENYL) propionyl chloride (109 mg, 0.55 mmol) and MECN (3.5 mL). The mixture was stirred at room temperature overnight, POURED INTO HCL (AQ. , IM) AND EXTRACTED WITH ETOAC. THE COMBINED extracts were washed with NAHC03 (aq. , sat. ), dried over NA2C03 and concentrated. The sub-title compound was obtained by crystallisation of the residue from ETOAC/BENZENE (108 mg, 50 %).

Reference： [1]Patent: WO2005/5415,2005,A1 .Location in patent: Page/Page column 77

26
[ 15893-42-2 ]
[ 142873-59-4 ]
N-(3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-3-(4-methoxyphenyl)propionamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		EXAMPLE 15b N-[3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl]-3-(4-methoxyphenyl)propionamide By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and <strong>[15893-42-2]3-(4-methoxyphenyl)propionyl chloride</strong>, the title compound was synthesised according to Example 1b. Yield: 72%. Melting point: 188-191 C. (Ethyl acetate-hexane) 1H-NMR (CDCl3) δ: 0.99-1.01 (3H, m), 1.19-1.26 (6H, m), 1.48 (3H, s), 1.64-1.68 (3H, m), 1.99 (3H, s), 2.05-2.13 (5H, m), 2.65-3.04 (3H, m), 3.72-3.77 (3H, m), 4.08 (1H, s), 6.47-7.19 (9H, m).
72%		Example 15b N-[3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl]-3-(4-methoxyphenyl)propionamide By using 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine and <strong>[15893-42-2]3-(4-methoxyphenyl)propionyl chloride</strong>, the title compound was synthesised according to Example 1b. Yield: 72%. Melting point: 188-191ØC. (Ethyl acetate-hexane) 1H-NMR (CDCl3) δ: 0.99-1.01 (3H, m), 1.19-1.26 (6H, m), 1.48 (3H, s), 1.64-1.68 (3H, m), 1.99 (3H, s), 2.05-2.13 (5H, m), 2.65-3.04 (3H, m), 3.72-3.77 (3H, m), 4.08 (1H, s), 6.47-7.19 (9H, m).

Reference： [1]Patent: US2002/160996,2002,A1
[2]Patent: EP1323716,2003,A1

27
[ 15893-42-2 ]
[ 113379-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In pyridine; methanol;	b) Preparation of 5-[3-(4-methoxyphenyl)propionyl]barbituric acid To a suspension of barbitunric acid (6.4 g) in 48 ml of pyridine are added dropwise 11 g of <strong>[15893-42-2]3-(4-methoxyphenyl)propionyl chloride</strong> and the mixture is stirred at room temperature for 18 hours. The reaction mixture is then poured into ice and acidified to pH=1 by adding 6 N hydrochloric acid. A solid precipitates, which is filtered and resuspended in methanol. The suspension is kept under stirring for 15 minutes, then the solid is recovered by filtration to give 12.2 g of the product. m.p. 248-250 C.

Reference： [1]Patent: US6110924,2000,A

28
[ 15893-42-2 ]
[ 17016-83-0 ]
4(S)-isopropyl-3-[3-(4-methoxyphenyl)-1-oxobutyl]-2-oxazolidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane;	PREPARATION 11 4(S)-Isopropyl-3-[3-(4-methoxyphenyl)-1-oxobutyl]-2-oxazolidinone 18.19 ml (29.1 mmoles) of butyllithium (as a 1.6M hexane solution) were added dropwise at -78 C. and under an atmosphere of nitrogen to a solution of 3.13 g (24.2 mmoles) of 4(S)-isopropyl-2-oxazolidinone in 50 ml of anhydrous tetrahydrofuran, and then the mixture was stirred for 30 minutes. At the end of this time, a solution of 5.43 g (29.1 mmoles) of <strong>[15893-42-2]3-(4-methoxyphenyl)propionyl chloride</strong> in 20 ml of anhydrous tetrahydrofuran was added dropwise to the resulting mixture over the course of 10 minutes. The mixture was then stirred for a further 1 hour, after which a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by medium pressure silica gel column chromatography (using a 1:3 by volume mixture of ethyl acetate and hexane as eluent), followed by recrystallization from diisopropyl ether, to give 5.63 g (yield 80%) of the title compound as white crystals, melting at 62.0-63.5 C. [α]D20 =+60.4 (C=1, chloroform). Elemental analysis: Calculated for C16 H21 NO4: C, 65.96%; H, 7.27%; N, 4.81%. Found: C, 65.98%; H, 7.25%; N, 4.75%. Mass spectrum (m/e): 291 (M+), 162, 134, 121. Infrared Absorption Spectrum (KBr) νmax cm-1: 1777, 1698.

Reference： [1]Patent: US5364844,1994,A

29
[ 15893-42-2 ]
[ 141-97-9 ]
[ 82782-33-0 ]

Yield	Reaction Conditions	Operation in experiment
28%	With hydrogenchloride; In water;	(ii) 5-(4-Methoxyphenyl)-3-oxopentanoic acid, ethyl ester 3-(4-Methoxyphenyl)propionyl chloride (84.6 g, 0.426 mole) was added to a stirred suspension of ethyl acetoacetate, sodium salt (64.7 g, 0.426 mole) in ether (250 ml) over a period of 1.5 hours and the reaction was allowed to sit for 16 hours. The reaction mixture was treated with water (100 ml) and extracted with ether. The ether extract was cooled in an ice bath and ammonia gas was bubbled into the solution for 2.5 hours while the reactants were allowed to warm to room temperature. The reaction was washed with water, filtered and the ether fraction was stirred with 3N hydrochloric acid (100 ml) for 16 hours. The ether layer was washed with water, 5% sodium bicarbonate, brine and dried with sodium sulfate. The solvent was removed and the residue was distilled under high vacuum to give the product as an yellow oil (30.0 g, 28%).

Reference： [1]Patent: US4798843,1989,A

30
[ 15893-42-2 ]
3-(4-Methoxy-phenyl)-propionyl azide [ No CAS ]

Reference： [1]Organic Letters,2008,vol. 10,p. 2601 - 2604
[2]Organic Letters,2014,vol. 16,p. 1268 - 1268

31
[ 864816-20-6 ]
[ 15893-42-2 ]
[ 1187591-42-9 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6519 - 6534

32
[ 15893-42-2 ]
[ 6638-79-5 ]
[ 749927-93-3 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 9610 - 9612

33
[ 15893-42-2 ]
[ 672-65-1 ]
[ 1433776-63-6 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

34
[ 2362-36-9 ]
[ 15893-42-2 ]
[ 1433777-19-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

35
[ 19935-78-5 ]
[ 15893-42-2 ]
[ 1433777-23-1 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

36
[ 20001-65-4 ]
[ 15893-42-2 ]
[ 1433777-35-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

37
[ 58464-06-5 ]
[ 15893-42-2 ]
[ 1433777-47-9 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

38
[ 15893-42-2 ]
[ 934-11-2 ]
[ 1433777-51-5 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

39
[ 15893-42-2 ]
[ 55631-12-4 ]
[ 1433777-54-8 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

40
[ 136904-76-2 ]
[ 15893-42-2 ]
[ 1433777-58-2 ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

41
[ 35275-62-8 ]
[ 15893-42-2 ]
[ 1433777-71-9 ]
(S)-1-(2,3-dihydro-1H-inden-1-yl)-3-(4-methoxyphenyl)propan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 7442 - 7445

42
[ 15893-42-2 ]
[ 1435490-42-8 ]
[ 1435490-50-8 ]

Yield	Reaction Conditions	Operation in experiment
14%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 5h;Inert atmosphere;	General procedure: A solution of the corresponding benzoyl chloride (0.3 mmol) in dry CH2Cl2 (5 mL) was added dropwise at 0 C to a stirred solution of N-methyl-1-pentanol-6,7-dimethoxy-1,2,3,4-THIQ 7 (88 mg, 0.3 mmol), 4-(dimethylamino)pyridine (12 mg, 0.1 mmol) and triethylamine (42 μL, 0.3 mmol) in dry CH2Cl2 (20 mL). The reaction mixture was stirred at room temperature under a N2 atmosphere for 5 h. Next, the reaction mixture was extracted with CH2Cl2 and washed with H2O. The organic layer was dried over anhydrous Na2SO4, filtered and evaporated to dryness. The residue was purified (toluene/AcOEt/MeOH 6:3:1) to obtain the corresponding THIQ ester.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 3221 - 3230

43
[ 15893-42-2 ]
[ 118-92-3 ]
[ 692281-53-1 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 120℃; for 0.0833333h;Microwave irradiation;	General procedure: To a solution of acyl chlorides (18.70 mmol) in anhydrous dichloromethane (20 mL) was added 2-amino-benzoic acid derivatives 4 (12.5 mmol). After the addition of pyridine (5 mL), the mixture was heated under microwave condition at 120 C for 5 min. The solvent was evaporated and the residue was diluted with 2 N HCl solution to induce the precipitation of a brown solid which was filtered, washed with water and dried under vacuum at 50 C, to afford the 2-acylamine-benzoic acids 5. A stirred solution of compounds 5 (25 mmol) in acetic anhydride (50 mL) was refluxed for 10 min. The solvent was removed in vacuum and the residue was taken up in diethyl ether, to provide after filtration and drying the title benzoxazin-4-ones 6. A solution of benzoxazin-4-ones 6 (20.2 mmol) and aminoguanidine hydrogencarbonate (20.2 mmol) in pyridine (25 mL) was heated under microwave condition at 180 C for 30 min. The reaction was cooled at room temperature and diluted with methanol/water 1:1 to induce the precipitation of a brown solid which was washed with a mixture MeOH/H2O 8:2, to afford the desired compounds

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 4135 - 4150

44
[ 15893-42-2 ]
3-methylbut-2-enyl-1,1-d2-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-oxobutanoate [ No CAS ]
3-methylbut-2-enyl-1,1-d2-2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-5-(4-methoxyphenyl)-3-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		3-Methylbut-2-enyl-1,1-d2-4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-oxobutanoate (71) (100 mg, 0.34 mmol, 1.0 equiv), MgCl2(64 mg, 0.67 mmol, 2.0 equiv), and pyridine (0.08 mL, 0.92 mmol,2.7 equiv) were stirred in CH2Cl2 (15 mL) at 0 C for 30 min. 3-(4-Methoxyphenyl)propanoyl chloride (81 mg, 0.41 mmol, 1.2 equiv)was added to the reaction mixture and stirring continued for 1 h at0 C and 2 h at 25 C. Reaction was quenched with brine (20 mL)and the mixture extracted with EtOAc (250 mL). The organic extractswere combined, dried (MgSO4), rotary evaporated, andchromatographed (2:8 Et2O/hexanes to Et2O) to give 3-methylbut-2-enyl-1,1-d2-2-(2-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)acetyl)-5-(4-methoxyphenyl)-3-oxopentanoate (40) (106 mg, 68%) asa yellow oil: Rf0.67 (2:1 Et2O/hexanes); IR (neat) nmax 1730, 1708,1640, 1514, 1500, 1392, 1375, 1273, 1246, 1205, 1177, 1038, 942,902 cm1; 1H NMR (CDCl3, 400 MHz) d 7.11 (d, J8.5 Hz, 2H), 6.83(d, J8.5 Hz, 2H), 5.37 (br s, 1H), 5.34 (s, 1H), 3.79e3.78 (m, 4H),3.68 (s, 2H), 3.00e2.97 (m, 2H), 2.92e2.89 (m, 2H),1.75 (d, J0.5 Hz,3H), 1.71 (d, J0.5 Hz, 3H), 1.69 (s, 6H); 13C NMR (CDCl3, 100 MHz)d 197.5,192.5,166.3,165.1,160.7,158.2,140.5,132.4,129.3 (2C),117.7,114.0 (2C), 108.7, 107.2, 96.4, 55.3, 42.8, 39.6, 31.0, 29.7, 25.7, 24.9(2C), 18.1; HRMS (ESI) calcd for C25H29D2O8, requires 461.2139,found 461.2137 (D0.4 ppm).

Reference： [1]Tetrahedron,2015,vol. 70,p. 5569 - 5579

45
[ 15893-42-2 ]
(R)-4-(phenylmethyl)-2-oxazolidinone [ No CAS ]
[ 1224714-08-2 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3191 - 3193

46
[ 15893-42-2 ]
(1R,2R)-1,2-diaminocyclohexane tartrate [ No CAS ]
N,N'-((1R,2R)-cyclohexane-1,2-diyl)bis(3-(4-methoxyphenyl)propanamide) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 7656 - 7659

47
[ 18978-78-4 ]
[ 15893-42-2 ]
3-(4-methoxyphenyl)-N-(2-methylquinolin-8-yl)propanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.5h;	[00418] 3-(4-Methoxyphenyl)propionyl chloride (199 mg, 1.0 mmol) was dissolved in dichloromethane (2 mL) and cooled to 0 C. This solution was added dropwise to a cooled (0C) solution of 8-aminoquinaldine (158 mg, 1.0 mmol) and N,N-diisopropylethylamine (260 jiL,1.5 mmol) in dichloromethane (5 mL). After addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hrs. The mixture was diluted with water and extracted with 2 volumes of dichloromethane. The organic layers were collected and the solvent was removed by rotary evaporation. The residue was purified by preparative reverse-phase HPLC using a water-acetonitrile gradient to afford compound A23. ESI-MS: m/z 321 [M+H].
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃; for 2.5h;	3-(4-Methoxyphenyl)propionyl chloride (199 mg, 1.0 mmol) was dissolved in dichloromethane (2 mL) and cooled to 0 C. This solution was added dropwise to a cooled (0 C.) solution of 8-aminoquinaldine (158 mg, 1.0 mmol) and N,N-diisopropylethylamine (260 μL, 1.5 mmol) in dichloromethane (5 mL). After addition was complete, the mixture was allowed to warm to room temperature and stirred for 2.5 hrs. The mixture was diluted with water and extracted with 2 volumes of dichloromethane. The organic layers were collected and the solvent was removed by rotary evaporation. The residue was purified by preparative reverse-phase HPLC using a water-acetonitrile gradient to afford compound A23. ESI-MS: m/z 321 [M+H]+.

Reference： [1]Patent: WO2016/32569,2016,A1 .Location in patent: Page/Page column 194
[2]Patent: US2019/151303,2019,A1 .Location in patent: Paragraph 0658

48
[ 15893-42-2 ]
[ 485-72-3 ]
3-(4-methoxyphenyl)-4-oxo-4H-benzopyran-7-yl 4-methoxy-3-phenylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66.8%	With pyridine; In dichloromethane; for 2h;Reflux;	A solution of p-methoxyphenylpropionic acid (12a, 2.99 mmol), SOCl2 (2 mL) and DMF (2 drops) was added to toluene (20 mL) and stirred at 75C for 3 h. The reaction was terminated and the solution was concentrated to dryness under reduced pressure to give p-methoxyphenylpropionyl chloride (13a)The 7-hydroxy-3- (4-methoxyphenyl) -4H-benzopyran-4-one(6,2.61 mmol), pyridine (1 mL) in CH2Cl2 (10 mL) was added dropwise with p-methoxyphenylpropionyl chloride (13a) with stirring. After completion of the dropwise addition, the reaction was refluxed for 2 h. The reaction was completed, cooled to room temperature, poured into dilute hydrochloric acid, stirred. Extracted with dichloromethane, and washed with saturated brine. The solvent was concentrated to dryness under reduced pressure to give crude product. Column chromatography (petroleum ether / ethyl acetate: 15/1, V / V) gave a white solid in 66.8%

Reference： [1]Patent: CN106146450,2016,A .Location in patent: Paragraph 0204; 0205; 0206

49
[ 15893-42-2 ]
[ 114671-83-9 ]
6-((tert-butyldiphenylsilyl)oxy)-1-(4-methoxyphenyl)hexane-3-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With manganese; FeBr2(1,2-bis(diphenylphosphino)benzene); lithium chloride; copper dichloride; In 1,2-dimethoxyethane; at 0℃; for 15h;	General procedure: To alkyl iodide la~q (1.2 equiv.), acid chloride 2a (1.0 equiv.) in 1,2- dimethoxyethane (C 0.4 M) were added manganese (2.0 equiv.), copper (II) chloride (1.0 equiv.), lithium chloride (3.0 equiv.) and FeBr2(dppb) 5a (5 mol%). The reaction mixture was cooled to 0 C and stirred vigorously for 15 h at the same temperature. Upon completion of reaction, florosil was added and stirred for 30 min at 0 C and filtered through a pad of Celite, washed with ethyl acetate (10 mL) and the filtrate was dried over anhydrous Na2S04, filtered and concentrated under rotary evaporator. After concentration, purification through a basic alumina column chromatography yields the desired ketone 3 a~q

Reference： [1]Organic Letters,2017,vol. 19,p. 2766 - 2769
[2]Patent: WO2019/9956,2019,A1 .Location in patent: Paragraph 00219; 00220; 00221; 00223

50
[ 15893-42-2 ]
[ 954412-31-8 ]
6-((tert-butyldiphenylsilyl)oxy)-1-(4-methoxyphenyl)-5-methylhexan-3-one [ No CAS ]