[ CAS No. 34837-88-2 ] {[proInfo.proName]}

Name: 34837-88-2|Methyl 2-(4-methoxy-3-nitrophenyl)acetate|98%
Brand: Ambeed
SKU: A326399
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Quality Control of [ 34837-88-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 34837-88-2 ]

Product Details of [ 34837-88-2 ]

CAS No. :	34837-88-2	MDL No. :	MFCD09754963
Formula :	C₁₀H₁₁NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HAFCSCBORMDMFL-UHFFFAOYSA-N
M.W :	225.20	Pubchem ID :	13846354
Synonyms :

Safety of [ 34837-88-2 ]

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

Application In Synthesis of [ 34837-88-2 ]

* 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 [ 34837-88-2 ]
Downstream synthetic route of [ 34837-88-2 ]

[ 34837-88-2 ] Synthesis Path-Upstream 1~10

1
[ 61873-93-6 ]
[ 74-88-4 ]
[ 34837-88-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	at 20℃;	N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-methyl-2-(2-(2-methylpyridin-3- yl)benzo[a) methyl 2-(4-methoxy-3-nitrophenyl)acetateTo a solution of methyl 2-(4-hydroxy-3-nitrophenyl)acetate (4.87 g, 23.1 mmol) at rt was added K₂CO₃ (8 g, 58 mmol), followed by slow addition of CH₃I (6.6 g, 46.5 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was then poured into ice-water (100 mL) and extracted with CH₂CI₂ (3 x 300 mL). The combined organic layers were washed with brine, dried over Na₂S0₄, filtered, and concentrated to afford the title compound (5 g, 96percent) as a yellow solid. LCMS-P1 : 226.0 [M+H]⁺; R_t: 1.438 min.

Reference： [1] Patent: WO2013/19682, 2013, A1, . Location in patent: Page/Page column 106; 107

2
[ 104-01-8 ]
[ 34837-88-2 ]

Reference： [1] Patent: US6630496, 2003, B1,
[2] Patent: WO2013/131408, 2013, A1,

3
[ 10463-20-4 ]
[ 74-88-4 ]
[ 34837-88-2 ]

Reference： [1] Patent: US2003/78251, 2003, A1,

4
[ 23786-14-3 ]
[ 34837-88-2 ]

Reference： [1] Patent: WO2013/131408, 2013, A1, . Location in patent: Page/Page column 63

5
[ 56245-07-9 ]
[ 34837-88-2 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1939, vol. 277, p. 271,281

6
[ 6378-19-4 ]
[ 34837-88-2 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1939, vol. 277, p. 271,281

7
[ 67-56-1 ]
[ 63304-80-3 ]
[ 34837-88-2 ]

Reference： [1] Archiv der Pharmazie (Weinheim, Germany), 1939, vol. 277, p. 271,281

8
[ 10463-20-4 ]
[ 34837-88-2 ]

Reference： [1] Patent: WO2013/19682, 2013, A1,

9
[ 156-38-7 ]
[ 34837-88-2 ]

Reference： [1] Patent: WO2013/19682, 2013, A1,

10
[ 186581-53-3 ]
[ 10463-20-4 ]
[ 34837-88-2 ]

Reference： [1] Chemistry of Natural Compounds, 1990, vol. 26, # 6, p. 691 - 696[2] Khimiya Prirodnykh Soedinenii, 1990, # 6, p. 811 - 818

[ 34837-88-2 ] Synthesis Path-Downstream 1~49

1
[ 67-56-1 ]
[ 63304-80-3 ]
[ 34837-88-2 ]

Reference： [1]Archiv der Pharmazie,1939,vol. 277,p. 271,281

2
[ 34837-88-2 ]
[ 63304-82-5 ]

Reference： [1]Synthetic Communications,2010,vol. 40,p. 661 - 665
[2]Archiv der Pharmazie,1939,vol. 277,p. 271,281

3
[ 186581-53-3 ]
[ 10463-20-4 ]
[ 34837-88-2 ]

Reference： [1]Chemistry of Natural Compounds,1990,vol. 26,p. 691 - 696
Khimiya Prirodnykh Soedinenii,1990,p. 811 - 818

4
[ 34837-88-2 ]
[ 168766-14-1 ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 411 - 415

6
[ 34837-88-2 ]
[ 110925-49-0 ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 411 - 415

7
[ 34837-88-2 ]
[ 110925-47-8 ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 411 - 415

8
[ 34837-88-2 ]
Toluene-4-sulfonic acid 2-(4-methoxy-3-nitro-phenyl)-ethyl ester [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 411 - 415

9
[ 34837-88-2 ]
N-[5-(2-Dipropylamino-ethyl)-2-methoxy-phenyl]-methanesulfonamide; hydrobromide [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1987,vol. 76,p. 411 - 415

10
[ 56245-07-9 ]
[ 34837-88-2 ]

Reference： [1]Archiv der Pharmazie,1939,vol. 277,p. 271,281

11
[ 6378-19-4 ]
[ 34837-88-2 ]

Reference： [1]Archiv der Pharmazie,1939,vol. 277,p. 271,281

12
[ 10463-20-4 ]
[ 74-88-4 ]
[ 34837-88-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 0.5h;	2-(4-hydroxy-3-nitrophenyl)acetic acid (10.0 g, 50 mmol) was dissolved in N,N-dimethylformamide (100 mL) and potassium carbonate (21.0 g, 152.2 mmol) was added into the solution. Methyl iodide (21.0 g, 147.9 mmol) was then added. The reaction mixture was warmed to 50 C. and reacted for 30 min. TLC showed the reaction was completed. The reaction mixture was slowly added into 300 mL of water, filtered, and the solid was washed with water and dried in vacua to give methyl 2-(4-methoxy-3-nitrophenyl)acetate (11.2 g, 49.8 mmol, yield: 98%). 1H NMR (400 MHz, DMSO-d6) delta 7.81 (d, J=2.4 Hz, 1H), 7.57 (dd, J=2.4 and 8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 3.91 (s, 3H), 3.75 (s, 2H), 3.63 (s, 3H); MS: 226.3 [M+H]+.
	In N,N-dimethyl-formamide;	(1) A mixture of 4-hydroxy-3-nitrophenylacetic acid (10 g, 50.7 mmol), sodium hydride (2.6 g, 0.11 mol), iodomethane (15.6 g, 0.11 mol) and N,N-dimethylformamide (170 ml) was stirred at room temperature overnight. The mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml). The extract was washed with 1 N aqueous sodium hydroxide solution, 5% potassium hydrogen sulfate, saturated aqueous sodium hydrogen sulfate and saturated saline, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane (1:1) to obtain methyl 2-(4-methoxy-3-nitrophenyl)acetate (10.4 g, 46.2 mmol, 91%) as colorless needles. Melting point 101-102 C. IR numax (KBr) cm-1: 1730 (C=O). 1H-NMR (CDCl3) delta: 3.626 (2H, s), 3.718 (3H, s), 3.960 (3H, s), 7.062 (1H, d, J=8.8 Hz), 7.478 (1H, dd, J=2.2, 8.8 Hz), 7.795 (1H, d, J=2.2 Hz). Elemental analysis (C10H11NO5) Cal'd: C, 55.58; H, 5.30; N, 4.96. Found: C, 53.44; H, 4.87; N, 5.98.

Reference： [1]Patent: US2019/152963,2019,A1 .Location in patent: Paragraph 0290; 0294-0296
[2]Patent: US2003/78251,2003,A1

13
[ 104-01-8 ]
[ 34837-88-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; nitric acid; acetic anhydride;	Step 1 Methyl 2-(3-Nitro4-methoxyphenyl)acetate An oven-dried 2-L, 3-neck round bottom flask, equipped with a mechanical stir motor, a low-temperature thermometer and an equalizing dropping funnel, was charged with acetic anhydride (631 mL) and subsequently cooled to -78 C. Fuming nitric acid (Baker, 90%, 27 mL) was added dropwise via the dropping funnel protected with a drying tube filled with CaCl2. After addition was completed, the reaction temperature was allowed to warm to 20 C. over 1 h. The reaction mixture was cooled to -78 C. again and added 4-methoxyphenylacetic acid (50 g, 0.28 mol) dropwise via the dropping funnel. After stirring at -50 C. for 1 h., the reaction mixture was allowed to warm to -30 C. over 20 min. and then cooled to -50 C. again. The reaction mixture was quenched with H2O (500 mL) at -50 C. and warmed up to room temperature and stirred for 0.5 h. The reaction mixture was partitioned between CH2Cl2 (500 mL) and H2O. The aqueous layer was extracted with CH2Cl2 (3500 mL). The combined CH2Cl2 extracts were concentrated in vacuo to give a yellow oil. This was added slowly to a 2 M solution of NaOH (2 L) cooled at 0 C. and stirred at room temperature overnight. The reaction mixture was partitioned between CH2Cl2 (500 mL) and H2O. The aqueous layer was extracted with CH2Cl2 (3500 mL). The combined CH2Cl2 extracts were stirred with 2 M NaOH solution (1 L) for 1 h. The layers were separated and the organic layer was washed with H2O (500 mL), brine (500 mL), dried over Na2SO4 and filtered. The solvents were removed in vacuo to afford crude product as a light yellow solid (56 g). Purification by recrystallization from MeOH (600 mL) gave product. Yield 48 g (77%).

Reference： [1]Patent: US6630496,2003,B1
[2]Patent: WO2013/131408,2013,A1

14
[ 10463-20-4 ]
[ 34837-88-2 ]

Reference： [1]Patent: WO2013/19682,2013,A1

15
[ 61873-93-6 ]
[ 74-88-4 ]
[ 34837-88-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; at 20℃;	N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-methyl-2-(2-(2-methylpyridin-3- yl)benzo[a) methyl 2-(4-methoxy-3-nitrophenyl)acetateTo a solution of methyl 2-(4-hydroxy-3-nitrophenyl)acetate (4.87 g, 23.1 mmol) at rt was added K2CO3 (8 g, 58 mmol), followed by slow addition of CH3I (6.6 g, 46.5 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was then poured into ice-water (100 mL) and extracted with CH2CI2 (3 x 300 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated to afford the title compound (5 g, 96%) as a yellow solid. LCMS-P1 : 226.0 [M+H]+; Rt: 1.438 min.

Reference： [1]Patent: WO2013/19682,2013,A1 .Location in patent: Page/Page column 106; 107

16
[ 34837-88-2 ]
[ 74-88-4 ]
[ 383671-69-0 ]

Yield	Reaction Conditions	Operation in experiment
39%		To a solution of <strong>[34837-88-2]methyl 2-(4-methoxy-3-nitrophenyl)acetate</strong> (4.6 g, 20.4 mmol) in THF (100 mL) at rt was added NaH (60%,2.5 g,62.5 mmol) slowly. The reaction mixture was stirred at rt for 2 h. CH3I (14.5 g, 102.1 mmol) was added slowly at rt, and the reaction mixture was stirred at rt overnight. The reaction mixture was cooled to 0 C and poured into saturated NH4C1 (100 mL). The reaction mixture was extracted with CH2CI2 (3 x 300 mL). The combined organic layers were washed with brine, dried over Na2S04, filtered, and concentrated. The resultant residue was purified by column chromatography (1 : 10 EtO Ac/petroleum ether) to provide the title compound (2 g, 39%). LCMS-P1 : 254.0 [M+H]+; Rt: 1.58 min.

Reference： [1]Patent: WO2013/19682,2013,A1 .Location in patent: Page/Page column 107

17
[ 156-38-7 ]
[ 34837-88-2 ]

Reference： [1]Patent: WO2013/19682,2013,A1
[2]Patent: US2019/152963,2019,A1

18
[ 23786-14-3 ]
[ 34837-88-2 ]

Reference： [1]Patent: WO2013/131408,2013,A1 .Location in patent: Page/Page column 63

19
[ 34837-88-2 ]
[ 171056-70-5 ]

Reference： [1]Patent: WO2013/131408,2013,A1

20
[ 34837-88-2 ]
[ 61873-93-6 ]

Reference： [1]Patent: WO2013/131408,2013,A1 .Location in patent: Page/Page column 64

21
[ 34837-88-2 ]
[ 78587-72-1 ]

Reference： [1]Patent: WO2013/131408,2013,A1

22
[ 34837-88-2 ]
[ 1455471-56-3 ]

Reference： [1]Patent: WO2013/131408,2013,A1

23
[ 34837-88-2 ]
[ 245095-55-0 ]

Reference： [1]Patent: WO2013/131408,2013,A1

24
[ 34837-88-2 ]
[ 1455471-57-4 ]

Reference： [1]Patent: WO2013/131408,2013,A1

25
[ 34837-88-2 ]
[ 134997-91-4 ]

Reference： [1]Patent: WO2013/131408,2013,A1

26
[ 34837-88-2 ]
[ 1455471-90-5 ]

Reference： [1]Patent: WO2013/131408,2013,A1

27
[ 34837-88-2 ]
[ 866038-49-5 ]

Reference： [1]Patent: WO2013/131408,2013,A1

28
[ 34837-88-2 ]
4-(4-methoxy-3-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiole-3-thione [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

29
[ 34837-88-2 ]
4-(3-amino-4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiole-3-thione [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

30
[ 34837-88-2 ]
4-(4-methoxy-3-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiol-3-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

31
[ 34837-88-2 ]
4-(3-amino-4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiol-3-one [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

32
[ 34837-88-2 ]
4-(4-methoxy-3-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiol-3-one oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

33
[ 34837-88-2 ]
4-(3-amino-4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiole-3-one oxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

34
[ 34837-88-2 ]
4-(4-methoxy-3-nitrophenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiol-3-one O-methyloxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

35
[ 34837-88-2 ]
4-(3-amino-4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-3H-1,2-dithiole-3-one O-methyloxime [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

36
[ 34837-88-2 ]
[ 118-41-2 ]
C₂₀H₂₁NO₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: CDI (8.63 mmol) was added to a round-bottomed flask containing compound 8 (5.08 mmol) and anhydrous DMF, and the mixture was stirred vigorously for 30 min at room temperature. Subsequently, the flask was placed in an ice bath, and methyl phenyl acetates 7 (5.33 mmol) and NaH (17.76 mmol) were added. The reaction was stirred for 4 h, the mixture was poured into a saturated solution of NH4Cl(aq) until pH = 7 was reached, and it was extracted with AcOEt. The combined organic phases were washed with a saturated solution of NaCl(aq) and dried over anhydrous MgSO4. After filtration, the organic solvent was removed under reduced pressure. The crude residue was purified by column chromatography using petroleum ether/ethyl acetate (2:1) as the eluent to yield purified compounds 9a-9e.

Reference： [1]European Journal of Medicinal Chemistry,2016,vol. 122,p. 520 - 529

37
[ 34837-88-2 ]
[ 63304-80-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20℃; for 1h;	Methyl 2-(4-methoxy-3-nitrophenyl)acetate (8.0 g, 35.6 mmol) was dissolved in tetrahydrofuran (80 mL) and water (20 mL). Lithium hydroxide monohydrate (4.5 g, 106.7 mmol) was slowly added to the reaction solution, and the reaction was stirred at room temperature for 1 hour. Tetrahydrofuran was removed under reduced pressure and the pH was adjusted to 3 with hydrochloric acid (3N). The reaction mixture was stirred for 15 minutes and then filtered. The filter cake was washed with 50 mL of water and dried to give 2-(4-methoxy-3-nitrophenypacetic acid. (6.0 g, 28.4 mmol, yield: 80%). 1H NMR (400 MHz, DMSO-d6) delta 12.46 (m, 1H), 7.79 (d, J=2.4 Hz, 1H), 7.56 (dd, J=2.4 and 8.8 Hz, 1H), 7.32 (d), J=8.8 Hz, 1H), 3.91(s, 3H), 3.64(s, 2H).

Reference： [1]Patent: US2019/152963,2019,A1 .Location in patent: Paragraph 0290; 0297-0299

38
[ 34837-88-2 ]
[ 857544-00-4 ]