2-Chloropyridine → 2-(N-Methyl-N-(2-pyridyl)amino)ethanol

HRID 1058088Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][NH:9][CH2:10][CH2:11][OH:12]>>[CH3:8][N:9]([CH2:10][CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

Reactant 2

HCID 79772-Chloropyridine

HCID 80162-(Methylamino)ethanol

Product 1

HCID 7374202-(N-Methyl-N-(2-pyridyl)amino)ethanol

Procedure

The reaction of 2-chloropyridine with 2-(N-methyl amino)ethanol provides 2-(N-methyl-N-(2-pyridyl)amino)ethanol (II), which on coupling reaction with 4-fluorobenzaldehyde (III) in an aprotic polar solvent with an alkali metal hydroxide or an alkali metal alkoxide as base yields 4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzaldehyde (IV) with an 88% yield (Reaction I).

Sources & evidence

ORD record: ord-e58b72df1612415e90e00bb4f473b1d1
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06515132B2

Reaction notes

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