109902-33-2

Basic information

• Product Name: 2-chloro-3-pivaloylaminopyridine
• Synonyms: 2-chloro-3-pivaloylaminopyridine
• CAS NO: 109902-33-2
• Molecular Formula: C₁₀H₁₃ClN₂O
• Molecular Weight: 213
• Mol File: 109902-33-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-chloro-3-pivaloylaminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-3-pivaloylaminopyridine(109902-33-2)
• EPA Substance Registry System: 2-chloro-3-pivaloylaminopyridine(109902-33-2)

Safety Data

• Hazardous Substances Data: 109902-33-2(Hazardous Substances Data)

Upstream product

• 6298-19-7 2-chloro-3-aminopyridine 
• 3282-30-2 pivaloyl chloride 
• 24331-71-3 N,N-dimethylpivalamide 

Downstream Products

• 209798-44-7 2-styryl-3-pivaloylamidopyridine 
• 143621-35-6 3-aminopyridine-2-carboxaldehyde thiosemicarbazone 
• 131653-73-1 2-chloro-4-phenyl-3-pivaloylaminopyridine 
• 142643-45-6 2-<2-(4-phenyl-3-pivaloylamino)pyridyl>quinoline 

Relevant articles and documents

3H-1,3-Azaphospholo[4,5-b]pyridines-novel heterocyclic P,N-bridging or hybrid ligands: Synthesis and first d8-transition metal complexes

The first 3H-1,3-azaphospholo-pyridines 2a-c were synthesized as racemic mixtures in modest to medium yield by the reaction of N-(2-chloropyrid-3-yl)-trimethylacetimidoyl chloride 1 with RPLi2 (R = Ph, n-Bu, i-Bu), generated from RPH2/sub

Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)

Palladium-catalyzed cross-coupling of methylboronic acid with 2-chloro- 3-nitropyridine produced 2-methyl-3-nitropyridine 4 in one step in high yield. Oxidation of 4 with selenium dioxide gave aldehyde 5. Alternatively, condensation of 4 with DMFDMA followed by oxidation gave 5 in a two step higher yielding conversion. Subsequent direct coupling of 5 with thiosemicarbazide followed by reduction of the nitro group using stannous chloride or sodium sulfide provided 3-AP (3). Reduction with sodium hydrosulfite gave 3-HAP (8). Finally a route which avoids the reduction of a nitro function was devised. Thus direct coupling of styrene with 2-chloro-3- aminopyridine 9 under Heck reaction conditions gave 16 which was converted to 17, oxidized to the aldehyde 18 and converted to 3-AP (3) with in situ deblocking of the t-Boc functionality.