22600-30-2|Methyl 5-aminofuran-2-carboxylate| Ambeed

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Quality Control of [ 22600-30-2 ] Purity: 98% SDS Specification

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Product Details of [ 22600-30-2 ]

CAS No. :	22600-30-2
Formula :	C₆H₇NO₃
M.W :	141.12
SMILES Code :	O=C(C1=CC=C(N)O1)OC
MDL No. :	MFCD00051661
InChI Key :	KLKQGSISBRVCTK-UHFFFAOYSA-N
Pubchem ID :	5072225

Safety of [ 22600-30-2 ]

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

Application In Synthesis of [ 22600-30-2 ]

* 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.

Downstream synthetic route of [ 22600-30-2 ]

[ 22600-30-2 ] Synthesis Path-Downstream 1~35

1
[ 22600-30-2 ]
[ 78-09-1 ]
[ 110189-96-3 ]

References: [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2817 - 2825.

2
[ 22600-30-2 ]
[ 109830-63-9 ]
[ 110189-98-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2826 - 2829.

3
[ 22600-30-2 ]
[ 109830-64-0 ]
[ 110190-05-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2826 - 2829.

4
[ 22600-30-2 ]
[ 122-51-0 ]
[ 109830-63-9 ]
[ 110189-98-5 ]

References: [1]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2817 - 2825.
[2]Collection of Czechoslovak Chemical Communications,1986,vol. 51,p. 2817 - 2825.

5
[ 1874-23-3 ]
[ 22600-30-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium 10% on activated carbon; In ethyl acetate; at 20℃; under 760.051 Torr; for 2h;	A solution of 100 mg of methyl 5-nitro-2-furoate (Lancaster Synthesis, Windham, N.H., USA) in 20 ml of EtOAc was stirred with 20 mg of Pd/C (10%) under one atmospheric pressure of hydrogen gas. After at RT for 2 hours, the mixture was filtered through a celite pad and concentrated. Pure methyl 5-amino-2-furoate was obtained by purification on a fresh silica gel column eluted with 30% EtOAc in hexane.
4.03 g	With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 18h;	Pd/C 10% wet (2.5 g) was added to a solution of methyl-5-nitrofuran-2-carboxylate (5 g, 29.2 mmol) in EtOH (50 mL) and the reaction mixture was hydrogenated at rt for 18h under atmospheric pressure. Then the catalyst was filtered off and the filtrate concentrated in vacuum to give a dark red solid (4.03 g, 28.6 mmol). LC (Method F): 1.059 min. LCMS: Anal. Calcd. for C6H7NO3: 141.02, found: 142.04 (M+1)+; 1H NMR (600 MHz, CDCl3) δ ppm 7.03 (d, J= 3.6Hz, 1H), 5.20 (d, J=3.6Hz, 1H), 4.55 (sb, 2H), 3.75 (s, 3H).
	With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 2h;	Dissolve 4-18 (171mg, 1mmol) in methanol (10mL), add Pd/C (10%, 17mg),Place in a hydrogenator to react at room temperature for 2 hours, and TLC (PE:EA=3:1) detects that the reaction is complete.The reaction solution was filtered through Celite, and the filtrate was concentrated to obtain a yellow oil (3-27).

References: [1]Organic Letters,2005,vol. 7,p. 5087 - 5090.
[2]Synthesis,2006,p. 3316 - 3340.
[3]Helvetica Chimica Acta,2002,vol. 85,p. 4485 - 4517.
[4]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1283 - 1287.
[5]Advanced Synthesis and Catalysis,2020,vol. 362,p. 314 - 319.
[6]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.
[7]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.
[8]Patent: US2005/256030,2005,A1 .Location in patent: Page/Page column 30.
[9]Patent: WO2013/163244,2013,A1 .Location in patent: Paragraph 00260.
[10]Patent: CN112107568,2020,A .Location in patent: Paragraph 0317-0320.

6
[ 22600-30-2 ]
[ 87-13-8 ]
[ 170959-84-9 ]

References: [1]Journal of Heterocyclic Chemistry,1995,vol. 32,p. 1283 - 1287.

7
[ 941-69-5 ]
[ 22600-30-2 ]
7-amino-1,3-dioxo-2-phenyl-2,3-dihydro-1H-isoindole-4-carboxylic acid methyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.
[2]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.

8
[ 22600-30-2 ]
[ 4358-59-2 ]
4-amino-1-hydroxy-2-methylcyclohexa-3,5-diene-1,3-dicarboxylic acid dimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.

9
[ 22600-30-2 ]
[ 5535-48-8 ]
[ 177913-38-1 ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.

10
[ 22600-30-2 ]
3-Hydroxy-6-imino-cyclohexa-1,4-diene-1,2,3-tricarboxylic acid trimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.

11
[ 22600-30-2 ]
[ 624-48-6 ]
4-amino-1-hydroxy-cyclohexa-3,5-diene-1,2,3-tricarboxylic acid trimethyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.

12
[ 22600-30-2 ]
[ 78-94-4 ]
[ 177913-49-4 ]

Yield	Reaction Conditions	Operation in experiment
44%	In benzene; for 1h;Heating / reflux;	5-Amino-furan-2-carboxylic acid methyl ester (0.42 g, 3.0 mmol) were mixed together with methyl vinyl ketone (10 ml.) in benzene and heated at reflux for 1 h. Evaporation of solvents were followed by flash chromatography using DCM / MeOH (95:5) as eluent to yield 44% (278 mg. 1.31 mmol) of 5-Acetyl-4-amino-1-hydroxy-cyclohexa-2,4-dienecarboxylic acid methyl ester. This compound were mixed with BF3 OEt2 ((284 mg, 2.0 mmol) in benzene (15 ml.) and refluxed for 0.5 h. The reaction mixture was quenched with NaHCO3 (sat) and extracted with dichloromethane. A precipitation formed in the organic phase was collected and confirmed to be the product by characterization with LC-MS and 1H NMR. Yield: 127 mg (50%).

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.
[3]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 1307 - 1324.
[4]Patent: WO2006/64286,2006,A1 .Location in patent: Page/Page column 117.

13
[ 22600-30-2 ]
[ 107-13-1 ]
4-amino-5-cyano-1-hydroxycyclohexa-2,4-dienecarboxylic acid methyl ester [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.
[2]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.

14
[ 22600-30-2 ]
[ 292638-85-8 ]
[ 177913-48-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	In dichloromethane; ethyl acetate; benzene;	1st Stage: Dimethyl 4-amino-1-hydroxycyclohexa-3,5-diene-1,3-dicarboxylate 526 ml of benzene and 250 ml of methyl acrylate are introduced into a 1-liter three-necked flask fitted with a reflux condenser, placed under inert atmosphere and protected from moisture, followed by 10 g (70.8 mmol) of <strong>[22600-30-2]methyl 5-amino-2-furoate</strong>. The mixture is brought to reflux and maintained for 24 hours. The reaction medium is concentrated to dryness at 50 C. under a vacuum of 20 mm Hg. The residue obtained is purified by flash chromatography using dichloromethane progressively enriched with ethyl acetate as solvent. The product is obtained as follows: Weight=15 g of a yellow precipitate, yield=93%, TLC: CH2Cl2/EtOAc 70/30 v/v Rf=0.35, m.p.=101.3 C., NMR: CDCl3 1H δ(ppm) 2.87 (d,1h); 2.93 (d,1H); 3.20 (s,1H); 3.71 (s,3H); 3.82 (s,3H); 6.02 (d,1H); 5.60-6.40 (brs,2H); 6.17 (d,1H)
93%	In dichloromethane; ethyl acetate; benzene;	Step 1-3 Dimethyl 4-amino-1-hydroxycyclohexa-3,5-diene-1,3-dicarboxylate 526 ml of benzene and 250 ml of methyl acrylate are introduced into a 1-liter three-necked flask fitted with a reflux condenser, placed under inert atmosphere and protected from moisture, followed by 10 g (70.8 mmol) of methyl 5-amino-2-furan carboxylate. The mixture is brought to reflux and maintained for 24 hours. The reaction medium is concentrated to dryness on a rotavapor at 50 C. under a vacuum of 20 mm Hg. The residue obtained is purified by flash chromatography using dichloromethane progressively enriched with ethyl acetate as solvent. The product is obtained as follows: Weight=15 g of a yellow precipitate Yield=93% TLC: CH2Cl2/EtOAc 70/30 v/v Rf=0.35 m.p.=101.3 C. NMR: CDCl3 1H δ(ppm) 2.87 (d,1H); 2.93 (d,1H); 3.20 (s,1H); 3.71 (s,3H); 3.82 (s,3H) 6.02 (d,1H); 5.60-6.40 (brs,2H); 6.17 (d,1H)

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 2880 - 2894.
[2]Patent: US2003/78276,2003,A1 .
[3]Patent: US2002/193377,2002,A1 .
[4]Tetrahedron Letters,1996,vol. 37,p. 2903 - 2906.
[5]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.

15
[ 22600-30-2 ]
methyl crotonate [ No CAS ]
4-amino-1-hydroxy-2-methylcyclohexa-3,5-diene-1,3-dicarboxylic acid dimethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 4088 - 4096.

16
[ 22600-30-2 ]
[ 39716-58-0 ]
[ 208334-93-4 ]