28179-47-7|3-Amino-5-(methoxycarbonyl)benzoic acid| Ambeed

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Quality Control of [ 28179-47-7 ] Purity: 97% SDS Specification

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Product Details of [ 28179-47-7 ]

CAS No. :	28179-47-7
Formula :	C₉H₉NO₄
M.W :	195.17
SMILES Code :	O=C(O)C1=CC(C(OC)=O)=CC(N)=C1
MDL No. :	MFCD00224870
Boiling Point :	No data available
InChI Key :	QGGKQIDRZUUHAR-UHFFFAOYSA-N
Pubchem ID :	13557643

Safety of [ 28179-47-7 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 28179-47-7 ]

* 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 [ 28179-47-7 ]

[ 28179-47-7 ] Synthesis Path-Downstream 1~27

1
[ 1955-46-0 ]
[ 28179-47-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen;palladium dihydroxide; In methanol; under 2585.81 Torr; for 5.0h;	EXAMPLE 14 Methyl 5-((lR,2S)-2-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidine- <n="88"/>l-carbonyl)cyclohexylcarbamoyl)biphenyl-3-carboxylateStep 1 : Preparation of 3-amino-5-(methoxycarbonyl)benzoic acid[00142] 20% Pd(OH)2 (0.50 g) was carefully wetted down under argon with methanol (5 mL) and then 3-(methoxycarbonyl)-5-nitrobenzoic acid (5.00 g, 22.2 mmol) in methanol (20 mL) was added. The mixture was then hydrogenated on a Parr Shaker apparatus for 5 hours at 50 psi. Under argon, the reaction was carefully filtered through a fiberglass filter paper. The filtrate was concentrated to give 3- amino-5-(methoxycarbonyl)benzoic acid (4.0 g, 20.5 mmol, 92% yield) of off-white solids as product. MS found: (M - H)+ = 194.
82%	With hydrogen;palladium 10% on activated carbon; In methanol; under 2585.81 Torr; for 3.0h;	A suspension of 3-(methoxycarbonyl)-5-nitrobenzoic acid (11.25 g, 50 mmol) and palladium on carbon (10 wt %, 1.0 g) in MeOH (10 mL) was shaken in hydrogenator under hydrogen at 50 psi for 3 h. The mixture was filtered and concentrated in vacuo to give the title compound (8.0 g, 82% yield): 1H NMR (CD3OD, 500 MHz) delta ppm 3.91 (3H, s), 7.53 (1H, m), 7.55 (1H, m), 7.92 (1H, m). HPLC retention time: 0.922 min (method A). MS (ESI) (M+H)+196.12.
71%	With hydrogen;5% palladium over charcoal; In methanol; at 20℃; under 2585.81 Torr; for 2.5h;	30.0 g (133.2 mmol) monomethyl 5-nitro-isophthalate were dissolved in 200 ml of methanol and combined with 3.0 g Pd/C (5%). The mixture was hydrogenated for 2.5 hours in a Parr apparatus at ambient temperature under a hydrogen pressure of 50 psi. Then the catalyst was filtered off and the filtrate was evaporated down i. vac. Yield 18.4 g (71%) 6.3-a. RT(HPLC 1)=2.88 min

	With hydrogenchloride;palladium; In tetrahydrofuran; diethyl ether;	Preparation of 3-Amino-5-(methoxycarbonyl)benzoic Acid (Compound 68) To 2.75 g of mono-methyl 5-nitroisophthalate (5-(methoxycarbonyl)-3-nitrobenzoic acid), compound 67, dissolved in 30 mL of THF was added 100 mg of 10% palladium on carbon. The reaction was placed in a Parr hydrogenator under a H2 atmosphere of 45 psi and shaken for 16 hr. The solid palladium catalyst was removed by vacuum filtration through celite and 5 mL of 1N HCl in diethyl ether was added to the filtrate. After sitting for 12 hr, the solid was collected by vacuum filtration and was washed with ethyl acetate. This provided 1.82 g of the desired product. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.
	With hydrogen;palladium on activated charcoal; In tetrahydrofuran; methanol; under 750.075 Torr;	Monomethyl-5-nitroisophthalate (50 g, 220 mmol, 1 eq) is dissolved in a mixture of 650 ml of MeOH and 350 ml of THF. 3 g of Pd/C are added, and the reaction mixture is hydrogenated overnight under 1 bar of H2 and then filtered. The filtrate is concentrated, and the residue is dissolved in a mixture of THF (200 ml) and aq NaHCO3 (400 ml). CbzCI (62 ml, 50% in toluene, 184 mmol, 0.9 eq) is added, the reaction mixture is stirred for 1 h, CbzCI (31 ml, 50% in toluene, 92 mmol, 0.45 eq) is added, and the reaction mixture is stirred overnight. The white solid formed is washed with water and diethyl ether to give the product.MS (ES-): 328 = [M-HT.HPLC (Nucleosil C18HD, 4x70 mm, 3 mum, 20-100% MeCN (6 min), 100% MeCN (1.5 min)) retention time: 4.36 min.1H-NMR (400 MHz, DMSO-d6): 8.40 (s, 1H), 8.38 (s, 1H), 8.17 (s, 1H), 7.50-7.37 (m, 5H),5.21 (s, 2H), 3.92 (s, 3H).
	With hydrogen;palladium on activated charcoal; In tetrahydrofuran; methanol; under 750.075 Torr;	a) 5-Benzyloxycarbonylamino-isophtalic acid monomethylesterMonomethyl-5-nitroisophtalate (50 g, 220 mmol, 1 eq) is dissolved in a mixture of 650 ml of MeOH and 350 ml of THF. 3 g of Pd/C are added, and the reaction is hydrogenated over night under 1 bar of hydrogen. The reaction mixture is then filtered and concentrated to give the amine as a crude product, which is then dissolved in a mixture of THF (200 ml) and <n="37"/>aqueous sodium bicarbonate (400 ml). CbzCI (62 ml, 50% in toluene, 184 mmol, 0.9 eq) are added to the reaction mixture, and the reaction is stirred for 1 hour. CbzCI (31 ml, 50% in toluene, 92 mmol, 0.45 eq) are added, and the reaction is stirred over night. The white solid which crashes out, is washed with water and diethyl ether to give the product. 1 H-NMR (400 MHz, dmso-d6): 8.40 (s, 1 H), 8.38 (s, 1 H), 8.17 (s, 1 H), 7.50-7.37 (m, 5H), 5.21 (s, 2H), 3.92 (s, 3H).
	With hydrogen;palladium on activated carbon; In methanol; under 2585.81 Torr; for 3.0h;	Step G (I): 3-ammo-5-(methoxycarbonyl)benzoic acid.; A suspension of 3-(methoxycarbonyl)-5-nitrobenzoic acid (20.0 g) and palladium on carbon (5 wt%, 4.0 g) in MeOH (600 mL) was shaken in hydrogenator under hydrogen at 50 psi for 3 h. The mixture was filtered and concentrated in vacuo to give the EPO <DP n="42"/>title compound: 1H NMR (CD3OD, 500 MHz) delta ppm 3.90 (3H, s), 7.52 (IH5 m), 7.55 (IH, m), 7.92 (IH, m). MS (ESI) (M-H)" 194.08.

References: [1]Patent: WO2009/15166,2009,A1 .Location in patent: Page/Page column 87.
[2]Chemical Communications,2012,vol. 48,p. 4809 - 4811.
[3]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2654 - 2660.
[4]Patent: US2007/32470,2007,A1 .Location in patent: Page/Page column 8-9.
[5]Patent: US2006/223759,2006,A1 .Location in patent: Page/Page column 193.
[6]Journal of the American Chemical Society,2003,vol. 125,p. 10241 - 10249.
[7]Patent: US6653321,2003,B1 .
[8]Patent: WO2007/77004,2007,A1 .Location in patent: Page/Page column 60.
[9]Patent: WO2008/9750,2008,A2 .Location in patent: Page/Page column 35-36.
[10]Patent: WO2006/99352,2006,A1 .Location in patent: Page/Page column 40-41.
[11]Organic and Biomolecular Chemistry,2013,vol. 11,p. 2693 - 2705.

2
[ 28179-47-7 ]
[ 161796-10-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With n-Butyl nitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 3.5h;	Step G (2): 3-bromo-5-(methoxycarbonyl)benzoic acid.; To a mixture of copper (II) bromide (5.5 g, 24.6 mmol), 7-butyl nitrite (3.17g, 30.75 mmol) and acetonitrile (300 mL) was added <strong>[28179-47-7]3-amino-5-(methoxycarbonyl)benzoic acid</strong> (Step G (1), 4.0 g, 20.5 mmol) in aceonitrile (300 mL) over 30 min at 0 0C and the mixture was warmed up and stirred at rt for 3 h. H2O was added and acetonitrile was removed. Ethyl acetate (600 mL) was added and the mixture was washed with 3N HCl, H2O, dried over Na2SO4, and concentrated in vacuo to give the title compound (97% yield): 1H NMR (CDCl3, 500 MHz) delta ppm 3.96 (3H, s), 8.41 (IH, s), 8.41 (IH, s), 8.67 (IH, m). MS (ESI) (M-HX 259.02.
68%		Step 2: Preparation of 3-bromo-5-(methoxycarbonyl)benzoic acid[00143] 3-Amino-5-(methoxycarbonyl)benzoic acid (1.0 g, 5.12 mmol, 1 eq.) was dissolved in 15% HBr (22.5 mL) at RT, then cooled to 0 0C with stirring. A 2.5 M aqueous solution OfNaNO2 (2.3 mL, 5.64 mmol, 1.1 eq.) was added slowly via an addition funnel to generate the diazonium salt. In a separate flask, CuBr was partially dissolved in 15% HBr (9 mL) and cooled to 0 0C with stirring, to which the <n="89"/>diazonium salt solution was subsequently added. A slight exotherm was observed. The reaction was stirred at RT for 30 minutes then carefully heated at 70 0C for 1 hour. The reaction was worked up by filtering off insoluble material as crude product. The solids were dissolved in water/EtOAc and the layers separated. The aqueous layer was extracted again with EtOAc. The organic layers were combined, dried over sodium sulfate and concentrated to give an off-white solid. The product was purified over silica gel in 1 : 1 hexanes/EtOAc to 100% EtOAc to 4: 1 methylene chloride/MeOH to yield 3-bromo-5-(methoxycarbonyl)benzoic acid (0.90 g, 3.47 mmol, 68% yield) as a white solid. MS found: (M - H)+ = 257/259.
34%	With n-Butyl nitrite; copper(ll) bromide; In acetonitrile; at 0 - 30℃; for 1.5h;	14.0 g (62.7 mmol) copper-(II)-bromide and 12.0 ml (102.6 mmol) n-butylnitrite in 300 ml acetonitrile were combined with 10.0 g (51.2 mmol) 6.3-a, suspended in 300 ml acetonitrile, while cooling with an ice bath. The reaction solution was stirred for 1.5 hours at 30 C., then evaporated to dryness i. vac. Then the residue was combined with dichloromethane and washed with 3N HCl and water. The organic phase was dried and evaporated to dryness using the rotary evaporator. The residue was combined with diethyl ether and the precipitate was filtered off. Yield 4.5 g (34%) 6.3-b. ES-MS (M+H)+=257/259 (bromine isotopes) RT(HPLC-MS)=2.87 min

With n-Butyl nitrite; copper(ll) bromide; In acetonitrile; at 0 - 20℃; for 1.41667h;

A mixture of copper (II) bromide (5.55 g, 24.9 mmol), n-butyl nitrite (3.21 g, 31.2 mmol) and acetonitrile (90 mL) was stirred in a round bottom flask at 0 C. 3-Amino-5-(methoxycarbonyl)benzoic acid (4.05 g, 20.77 mmol) was added as a slurry in warm aceonitrile (210 mL) over 25 min. and the mixture was stirred at room temeprature for 1 h. The mixture was concentrated and partitioned between dichloromethane and 3N hydrochloric acid. The organic layer was separated, dried over MgSO4, and concentrated in vacuo to give the title compound (5.3 g): 1H NMR (CD3OD, 500 MHz) delta ppm 3.97 (3H, s), 8.34-8.36 (2H, m), 8.58 (1H, m).

References: [1]Patent: WO2006/99352,2006,A1 .Location in patent: Page/Page column 41.
[2]Journal of the American Chemical Society,2003,vol. 125,p. 10241 - 10249.
[3]Patent: WO2009/15166,2009,A1 .Location in patent: Page/Page column 87-88.
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2654 - 2660.
[5]Patent: US2006/223759,2006,A1 .Location in patent: Page/Page column 193.
[6]Patent: US2007/32470,2007,A1 .Location in patent: Page/Page column 8-9.

3
[ 28179-47-7 ]
5-(methoxycarbonyl)-3'-nitro-1,1'-biphenyl-3-carboxylic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,2003,vol. 125,p. 10241 - 10249.

4
[ 28179-47-7 ]
[ 93116-99-5 ]

Yield	Reaction Conditions	Operation in experiment
55%		To an ice-cold, stirred solution of commercially available 3-amino-5- (methoxycarbonyl) benzoic acid (5.19 g, 26.59 mmol) in 2 N hydrochloric acid (156 mL) was added a solution of sodium nitrite (1.84 g, 26.67 mmol) in water (10.8 mL). This mixture was then added dropwise to an ice-cold, stirred solution of potassium iodide (8.84 g, 53.25 mmol) in water (26.2 mL). After stirring for 35 min, the reaction mixture was diluted with water <Desc/Clms Page number 175>and extracted with ethyl acetate. The organic layer was washed with5% aqueous sodium thiosulfate, and saturated sodium chloride, dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50 : 50 : 2 hexanes/ethyl acetate/acetic acid) afforded the title compound (4.48 g, 55% yield) as an off-white solid. ESI-MS (m/z) : 305 [M +H] +

References: [1]Patent: WO2004/22523,2004,A2 .Location in patent: Page 174-175.

5
[ 618-46-2 ]
[ 28179-47-7 ]
[ 325981-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; diethyl ether; water; ethyl acetate;	Preparation of 3-[(3-Chlorophenyl)carbonylamino]-5-(methoxycarbonyl)benzoic Acid (Compound 70) To 0.576 g (2.49 mmol) of compound 68 was added 10 mL of THF, 10 mL of water, and 2.6 mL of a 1N aqueous solution of sodium hydroxide. To this reaction solution was added, alternately in small portions, a solution of 341 muL (2.74 mmol) of 3-chlorobenzoyl chloride (compound 69) in 5 mL of THF and 2.6 mL of a 1N aqueous solution of sodium hydroxide. During the additions, the pH of the reaction solution was checked by pH paper and the reaction was kept at a pH greater than 8. After complete addition, TLC indicated some compound 68 remained. The above procedure was repeated using 150 muL (1.21 mmol) of 3-chlorobenzoyl chloride (69) in 5 mL THF and enough 1N aqueous sodium hydroxide to maintain a reaction solution pH above 8. After TLC analysis indicated complete consumption of compound 68, the reaction was extracted with ethyl acetate and 0.5 N aqueous sodium bicarbonate. Then, the aqueous layer was acidified with 6 N HCl and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and volatiles removed in vacuo. The resulting residue was treated with ethyl acetate/diethyl ether 50/50 to form a white solid that was collected by vacuum filtration. This provided 0.604 g of the desired product. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

References: [1]Patent: US6653321,2003,B1 .

6
[ 28179-47-7 ]
[ 153203-57-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With n-Butyl nitrite; copper dichloride; In acetonitrile; at 0 - 20℃; for 2.0h;	2.5 g (18.6 mmol) copper-(II)-chloride and 3.6 ml (30.8 mmol) n-butylnitrite were dissolved in 50 ml acetonitrile. While cooling with the ice bath a suspension of 3.0 g (15.4 mmol) 6.3-a in 150 ml acetonitrile was slowly metered in and the reaction solution was stirred for 2 hours at ambient temperature. After the reaction had ended the mixture was evaporated down i. vac., the residue was combined with dichloromethane and washed with 3N HCl and water. The organic phase was evaporated to dryness using the rotary evaporator, the residue was combined with diethyl ether, the precipitate was filtered off and dried. Yield 1.6 g (47%) beige crystals 9-a. ES-MS (M+H)+=215

References: [1]Patent: US2006/223759,2006,A1 .Location in patent: Page/Page column 201.

7
[ 501-53-1 ]
[ 28179-47-7 ]
[ 900799-65-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In tetrahydrofuran; water; toluene;	Monomethyl-5-nitroisophthalate (50 g, 220 mmol, 1 eq) is dissolved in a mixture of 650 ml of MeOH and 350 ml of THF. 3 g of Pd/C are added, and the reaction mixture is hydrogenated overnight under 1 bar of H2 and then filtered. The filtrate is concentrated, and the residue is dissolved in a mixture of THF (200 ml) and aq NaHCO3 (400 ml). CbzCI (62 ml, 50% in toluene, 184 mmol, 0.9 eq) is added, the reaction mixture is stirred for 1 h, CbzCI (31 ml, 50% in toluene, 92 mmol, 0.45 eq) is added, and the reaction mixture is stirred overnight. The white solid formed is washed with water and diethyl ether to give the product.MS (ES-): 328 = [M-HT.HPLC (Nucleosil C18HD, 4x70 mm, 3 mum, 20-100% MeCN (6 min), 100% MeCN (1.5 min)) retention time: 4.36 min.1H-NMR (400 MHz, DMSO-d6): 8.40 (s, 1H), 8.38 (s, 1H), 8.17 (s, 1H), 7.50-7.37 (m, 5H),5.21 (s, 2H), 3.92 (s, 3H).
	With sodium hydrogencarbonate; In tetrahydrofuran; water; toluene;	a) 5-Benzyloxycarbonylamino-isophtalic acid monomethylesterMonomethyl-5-nitroisophtalate (50 g, 220 mmol, 1 eq) is dissolved in a mixture of 650 ml of MeOH and 350 ml of THF. 3 g of Pd/C are added, and the reaction is hydrogenated over night under 1 bar of hydrogen. The reaction mixture is then filtered and concentrated to give the amine as a crude product, which is then dissolved in a mixture of THF (200 ml) and <n="37"/>aqueous sodium bicarbonate (400 ml). CbzCI (62 ml, 50% in toluene, 184 mmol, 0.9 eq) are added to the reaction mixture, and the reaction is stirred for 1 hour. CbzCI (31 ml, 50% in toluene, 92 mmol, 0.45 eq) are added, and the reaction is stirred over night. The white solid which crashes out, is washed with water and diethyl ether to give the product. 1 H-NMR (400 MHz, dmso-d6): 8.40 (s, 1 H), 8.38 (s, 1 H), 8.17 (s, 1 H), 7.50-7.37 (m, 5H), 5.21 (s, 2H), 3.92 (s, 3H).

References: [1]Patent: WO2007/77004,2007,A1 .Location in patent: Page/Page column 60.
[2]Patent: WO2008/9750,2008,A2 .Location in patent: Page/Page column 35-36.

8
[ 107-08-4 ]
[ 28179-47-7 ]
[ 1373965-82-2 ]