220559-34-2

Basic information

• Product Name: Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester
• Synonyms: Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester
• CAS NO: 220559-34-2
• Molecular Formula: C₁₃H₁₄Cl₂N₂O₃
• Molecular Weight: 0
• Mol File: 220559-34-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester(220559-34-2)
• EPA Substance Registry System: Furo[3,4-c]pyridine-1-carboxylic acid, 4,6-dichloro-3-(diethylamino)-, methyl ester(220559-34-2)

Safety Data

• Hazardous Substances Data: 220559-34-2(Hazardous Substances Data)

Upstream product

• 220559-31-9 N,N-diethyl-2,6-dichloro-4-methyl-3-pyridinamide 
• 91591-70-7 2,6-dichloro-4-methyl-3-pyridinecarboxaldehyde 
• 771579-84-1 C-(2,6-dichloro-4-methyl-pyridin-3-yl)-methylamine 
• 220559-32-0 methyl 2,6-dichloro-3-(N,N-diethylamido)pyridine-4-acetate 
• 62774-90-7 2,6-dichloro-4-methyl-nicotinic acid 
• 875-35-4 2,6-dichloro-4-methylnicotinonitrile 
• 56950-89-1 2,6-dichloro-4-methylnicotinoyl chloride 
• 220559-33-1 diazo-(2,6-dichloro-3-diethylcarbamoyl-pyridin-4-yl)-acetic acid methyl ester 

Relevant articles and documents

Synthesis and Reactions of a Stable o-Quinoid 10-π-Electron System, Furo[3,4-c]pyridine

Methyl 4,6-dichloro-3-(diethylamino)furo[3,4-c]pyridine-1-carboxylate (6), an intermediate in the Hamaguchi-Ibata reaction involving the RhII-catalyzed intramolecular reaction of a diazo group with the carbonyl of an adjacent amido group, has been isolated and characterized. PM3 calculations reveal the heat of formation (ΔHf) of this remarkably stable molecule to be -77.7 kcal/mol. Compound 6 undergoes a facile Diels-Alder cycloaddition with a variety of dienophiles to give polysubstituted isoquinoline derivatives via ring opening of initially formed cycloadducts. In each case the cycloaddition proceeds with high regioselectivity, with the electron-withdrawing group located ortho to the amino group. The most favorable FMO interaction is between the HOMO of the azaisobenzofuran 6 and the LUMO of the dienophile. The atomic coefficient at the ester carbon of the azaisobenzofuran 6 is larger than the amino center, and this nicely accommodates the observed regioselectivity.

Methyl 4,6-dichloro-3-diethylaminofuro[3,4-c]pyridine-1-carboxylate: Synthesis of the first stable azaisobenzofuran by a Hamaguchi-Ibata reaction

The title compound, an intermediate in the Hamaguchi-Ibata reaction involving the Rh(II)-catalysed intramolecular reaction of a diazo group with the carbonyl of an adjacent amido group has been isolated and characterized. PM3 calculations reveal the heat of formation(ΔH(f)) of this remarkably stable molecule to be -77.69 kcal/mol.