2142-04-3|2-(4-Methoxyphenyl)isoindoline-1,3-dione| Ambeed

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Quality Control of [ 2142-04-3 ] Purity: 95+% SDS Specification

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Product Details of [ 2142-04-3 ]

CAS No. :	2142-04-3
Formula :	C₁₅H₁₁NO₃
M.W :	253.25
SMILES Code :	O=C1N(C2=CC=C(OC)C=C2)C(C3=C1C=CC=C3)=O
MDL No. :	MFCD00429499
InChI Key :	ZETLVSOYHDFNPZ-UHFFFAOYSA-N
Pubchem ID :	250687

Safety of [ 2142-04-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 2142-04-3 ]

* 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 [ 2142-04-3 ]

[ 2142-04-3 ] Synthesis Path-Downstream 1~35

1
[ 85-44-9 ]
[ 104-94-9 ]
[ 2142-04-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With o-phthalimide-N-sulfonic acid; In ethanol; at 80℃; for 2h;Green chemistry;	General procedure: A mixture of phthalic anhydride (0.296 g, 2 mmol), amine (2.2 mmol), and phthalimide-N-sulfonic acid (0.091 g, 20 mol%) in ethanol (5 ml) was stirred for 3 h at 80 C. After completion (monitored by TLC), the insoluble catalyst was separated by filtration, washed with acetone, and dried (weight: 0.090 g, 99 % recovered). The organic layer was concentrated under reduced pressure to give the desired product, washed with water, and recrystallized in ethanol (each product was dissolved in a minimum amountof hot ethanol and allowed to reach gradually to room temperature). In addition, some products needed extrapurification step by small column chromatography using the CH2Cl2/n-hexane solvent mixture (50:50).
86%		General procedure: Phthalic anhydride (10 mmol) was added to the corresponding anilines (12 mmol) in dichloromethane (50 mL) for 30 min at room temperature, affording the corresponding 2-(arylcarbamoyl)benzoic acids. The products were obtained by vacuum filtration in almost quantitative yields. The solids were then dried and dissolved in acetic anhydride and heated at 90 C for 2-4 h with freshly fused anhydrous sodium acetate as the catalyst (15 mol%). The solvent was evaporated under vacuum, and the crude solids were dissolved in dichloromethane to filter off the insoluble sodium acetate. The organic solvent was evaporated under vacuum, and the solid thus obtained was recrystallized from methanol, affording N-aryl-1H-pyrrole-2,5-diones in a pure form.
	In water;Reflux;	General procedure: A mixture of 1 (10 mmol), 2 (10 mmol) in water (20 mL) was refluxed for 1.5-2 h. At the end of this period, a colourless solid separated out from the reaction mixture which was collected by filtration. The isolated solid was washed with water (10 mL) and dried. The crude product was recrystallized from a suitable solvent to obtain 5a-5l.

References: [1]Synlett,2002,p. 343 - 345.
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2004,vol. 43,p. 882 - 884.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2002,vol. 41,p. 1083 - 1085.
[4]Medicinal Chemistry Research,2014,vol. 23,p. 2736 - 2743.
[5]RSC Advances,2014,vol. 4,p. 59454 - 59461.
[6]Chemical Papers,2017,vol. 71,p. 2293 - 2299.
[7]Tetrahedron Letters,2016,vol. 57,p. 772 - 777.
[8]Journal of Organic Chemistry,2019,vol. 84,p. 3968 - 3976.
[9]Tetrahedron,1995,vol. 51,p. 4655 - 4664.
[10]Journal of the Chinese Chemical Society,2009,vol. 56,p. 839 - 842.
[11]Organic Letters,2017,vol. 19,p. 6404 - 6407.
[12]Journal of Organic Chemistry,2019,vol. 84,p. 1898 - 1907.
[13]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 327 - 336.
[14]International Journal of Chemical Kinetics,2004,vol. 36,p. 316 - 325.
[15]Chemische Berichte,1942,vol. 75,p. 1558,1567.
[16]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 261 - 272.
[17]Journal of general chemistry of the USSR,1984,vol. 54,p. 819 - 824.
Zhurnal Obshchei Khimii,1984,vol. 54,p. 919 - 925.
[18]Collection of Czechoslovak Chemical Communications,1999,vol. 64,p. 1709 - 1726.
[19]Organic Preparations and Procedures International,2013,vol. 45,p. 314 - 320.
[20]Chemical Communications,2014,vol. 50,p. 9273 - 9276.
[21]Letters in Organic Chemistry,2014,vol. 11,p. 768 - 773.
[22]CrystEngComm,2015,vol. 17,p. 2523 - 2528.

2
[ 136918-14-4 ]
[ 104-92-7 ]
[ 2142-04-3 ]

References: [1]Canadian Journal of Chemistry,1983,vol. 61,p. 86 - 91.

3
[ 615-42-9 ]
[ 201230-82-2 ]
[ 104-94-9 ]
[ 2142-04-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; under 760.051 Torr; for 4h;Schlenk technique;	General procedure: A 50 cm3 Schlenk flask was charged with an ortho-substituted iodoarene(1×10-3 mol), an amine (1.1-5×10-3 mol), K2CO3(2×10-3 mol), a catalyst (5×10-6 mol), and a stirring bar. Next, 5cm3 of DMF was added. Under balloon pressure of CO, the reactionmixture was stirred at 100 C for 1-6 h. After the reaction, the Schlenkflask was cooled down, and the organic products were extracted with3×7 cm3 of diethyl ether (3×15 min with stirring) and then GCanalyzed with dodecane as the internal standard (0.076 cm3, 5.46×10-4 mol). Each reaction was repeated minimum twice and the averagevalue from two experiments was reported. The difference between tworesults was below 5%.After the solvents were evaporated, the crude product was purifiedby flash chromatography on silica gel using hexane/ethyl acetate (10:4)as the eluent, and the corresponding N-substituted phthalimides wereobtained

References: [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 3415 - 3422.
[2]Applied Catalysis A: General,2018,vol. 560,p. 73 - 83.
[3]Journal of Organic Chemistry,1991,vol. 56,p. 6573 - 6579.
[4]Advanced Synthesis and Catalysis,2016,vol. 358,p. 314 - 320.

4
phenylmagnesium bromide [ No CAS ]
[ 2142-04-3 ]
[ 3532-69-2 ]

References: [1]Journal of general chemistry of the USSR,1984,vol. 54,p. 819 - 824.
Zhurnal Obshchei Khimii,1984,vol. 54,p. 919 - 925.

5
[ 2142-04-3 ]
[ 108444-19-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen; lithium hydroxide; In isopropyl alcohol; at 60℃; under 7500.75 Torr; for 24h;	Add 253 mg of 2- (4-methoxybenzene) isoindolin-1,3-dione (1 mmol), 10 mg of lithium t-butoxide, and 2 ml of isopropanol under nitrogen protection in a glass test tube with magnetons Then, 20 microliters of 0.01M catalyst (S / C = 5,000) was added, and 1 MPa of hydrogen was charged, and the reaction was carried out at 60 C for 24 hours. After the reaction was completed, the mixture was naturally cooled to room temperature, and the hydrogen gas was carefully released. The celite was filtered, and the filtrate was stripped of the organic solvent to obtain 250 mg of the product with a yield of 98%
80%	With methanol; sodium tetrahydroborate; In tetrahydrofuran; at 0 - 5℃; for 0.5h;	General procedure: Appropriate N-aryl-1H-pyrrole-2,5-diones were dissolved in THF (30 times). Then, the mixture was cooled in an ice bath to 0-5 C, and NaBH4 (1.0 equiv) was added in portions over 10 min (NaBH4 is insoluble in THF). Then, methanol (10 times) was added dropwise (H2 gas was evolved, and NaBH4 dissolved). The reaction progress was monitored by TLC. The reductionS4reaction took approximately 30 min for completion. Once the TLC showed only one single spot, a more polar compound than the starting material, the remaining NaBH4 was quenched by adding a dilute HCl solution (0.5 N) until pH 4. The solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate and water (three times). The organic layer was dried over anhydrous Na2SO4 and evaporated in vacuum to dryness, affording the pure products.

References: [1]Patent: CN110746342,2020,A .Location in patent: Paragraph 0043; 0044; 0045; 0046.
[2]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3024 - 3030.
[3]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 848 - 857.
[4]Tetrahedron Letters,2016,vol. 57,p. 772 - 777.
[5]Synthetic Communications,1998,vol. 28,p. 1281 - 1286.
[6]Chinese Journal of Chemistry,2010,vol. 28,p. 449 - 456.
[7]Molecules,2022,vol. 27.

6
[ 75-77-4 ]
[ 2142-04-3 ]
2-(4-Methoxy-phenyl)-1,3-bis-trimethylsilanyloxy-2H-isoindole [ No CAS ]

References: [1]Tetrahedron,1995,vol. 51,p. 4655 - 4664.

7
[ 73357-44-5 ]
[ 670-54-2 ]
2-(4-methoxyphenyl)-3-dicyanomethylene-2,3-dihydro-1H-isoindol-1-one [ No CAS ]
[ 2142-04-3 ]

References: [1]Tetrahedron,1995,vol. 51,p. 7451 - 7458.

8
[ 73357-44-5 ]
2-(4-methoxyphenyl)-3-dicyanomethylene-2,3-dihydro-1H-isoindol-1-one [ No CAS ]
[ 2142-04-3 ]

References: [1]Tetrahedron,1995,vol. 51,p. 7451 - 7458.

9
[ 85-44-9 ]
[ 2101-87-3 ]
[ 2142-04-3 ]

References: [1]Tetrahedron Letters,1998,vol. 39,p. 8733 - 8734.

10
[ 73357-44-5 ]
[ 1172-02-7 ]
[ 84409-01-8 ]
(4-amino-2,7-dinitro-9H-fluoren-9-ylidene)propane dinitrile [ No CAS ]
2-{(Z)-2,2'-Bis-(4-methoxy-phenyl)-3'-[(Z)-4-methoxy-phenylimino]-2',3'-dihydro-[1,1']biisoindolyliden-3-ylidene}-malononitrile [ No CAS ]
[ 2142-04-3 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 121 - 128.

11
[ 73357-44-5 ]
2-{(Z)-2,2'-Bis-(4-methoxy-phenyl)-3'-[(Z)-4-methoxy-phenylimino]-2',3'-dihydro-[1,1']biisoindolyliden-3-ylidene}-malononitrile [ No CAS ]
[ 2142-04-3 ]

References: [1]Journal of Heterocyclic Chemistry,1998,vol. 35,p. 121 - 128.

12
N-<4-methoxy-phenyl>-phthalimid, yellow form. [ No CAS ]
[ 2142-04-3 ]

References: [1]Chemische Berichte,1903,vol. 36,p. 999.
Gazzetta Chimica Italiana,1903,vol. 33 II,p. 8.

13
[ 7554-80-5 ]
[ 2142-04-3 ]

References: [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2001,p. 512 - 521.
[2]Organic Preparations and Procedures International,2013,vol. 45,p. 314 - 320.
[3]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1166 - 1171.
[4]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1166 - 1171.
[5]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1166 - 1171.
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1166 - 1171.
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 1166 - 1171.
[8]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2014,vol. 53,p. 392 - 398.
[9]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 848 - 857.

14
[ 136918-14-4 ]
[ 5720-07-0 ]
[ 2142-04-3 ]

References: [1]Synlett,2004,p. 1095 - 1097.
[2]Synlett,2006,p. 2290 - 2292.

15
[ 136918-14-4 ]
[ 33397-21-6 ]
[ 2142-04-3 ]

References: [1]RSC Advances,2016,vol. 6,p. 14531 - 14537.
[2]Synlett,2006,p. 2290 - 2292.

16
[ 610-97-9 ]
[ 5416-93-3 ]
[ 2142-04-3 ]

References: [1]Chemical Communications,2005,p. 4554 - 4556.

17
[ 2142-04-3 ]
[ 127935-43-7 ]