Pyridine → 2-Acetamido-3-methylpyridine

HRID 427217

Reaction equation

HRID 427217 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9](Cl)(=[O:11])[CH3:10].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:9][C:10]1[NH:1][C:2]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[CH:4][N:3]=2.[C:9]([NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1)(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 153472-Amino-3-methylpyridine

Product 2

HCID 2682952-Acetamido-3-methylpyridineHCID 5830662-Methyl-7-azaindole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-methyl-7-azaindole was prepared in two steps. First, 2-amino-3-picoline was reacted with acetyl chloride in toluene in the presence of pyridine to produce 2-acetamido-3-picoline in 65% yield. Second, pyrolysis of 2-acetamido-3-picoline in N-methylaniline in the presence of NaH at 280° C. was performed to produce 2-methyl-7-azaindole (FIG. 18) in 23% yield. This compound was characterized by NMR spectroscopy.

Sources & evidence

ORD record
ord-a4917c4c5f0c459ab8bd0167c09b9703
Source dataset
uspto-grants-2001_11
Patent number
US06312835B1

Linked notes

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