Ethanolamine → 6-(2-Hydroxyethylamino)nicotinaldehyde

Reaction equation

[NH2:1][CH2:2][CH2:3][OH:4].Cl[C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][N:7]=1>>[OH:4][CH2:3][CH2:2][NH:1][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][N:7]=1

Participants

Reactant 2

HCID 700Ethanolamine

HCID 27640536-Chloropyridine-3-carbaldehyde

Product 1

HCID 592786186-(2-Hydroxyethylamino)nicotinaldehyde

Conditions

Temperature: 135 °C

Procedure

10.12 g (165.68 mmol) of 2-aminoethanol are added to 1.00 g (7.06 mmol) of 6-chloronicotinaldehyde, and the reaction mixture is then stirred at 135° C. for 14 h. This gives a yellow solution which is fractionated by distillation in a kugelrohr apparatus (2.2 mbar, 100° C.). The fraction comprising the desired product is then directly reacted further.

Workup

customThis gives a yellow solution which
distillationis fractionated by distillation in a kugelrohr apparatus (2.2 mbar, 100° C.)
customis then directly reacted further

Sources & evidence

ORD record: ord-e17903c7cbdb474ea0511ea1ea6cc076
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653109B2

Reaction notes

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