Oxalic Acid → HCID 178483418, compound

HRID 489781Notes

Reaction equation

[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH3:4].[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17].CC(O)C>C(O)C>[C:15]([OH:20])(=[O:19])[C:16]([OH:18])=[O:17].[CH3:1][NH:2][CH:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][C:11]([OH:14])=[CH:12][CH:13]=1)[CH3:4]

Participants

Conditions

Temperature: 4 °C

Procedure

(4E)-N-Methyl-5-(6-hydroxy-3-pyridyl)-4-penten-2-amine (0.263 g of 91%, 1.23 mmol) was dissolved in warm absolute ethanol (3 mL) and combined with oxalic acid (0.110 g, 1.23 mmol) in warm absolute ethanol (4.5 mL). The solution was cooled at 4° C. for 1 h, during which time an oily material was deposited. The ethanol was evaporated to leave a dark brown oil, which was combined with 2-propanol (3 mL). This mixture (heterogeneous) was refluxed as absolute ethanol was added drop-wise. Once homogeneous, the mixture was cooled to ambient temperature as the walls of the flask were scratched with a spatula. A tan precipitate formed. The mixture was kept at 4° C. overnight and filtered. The filter cake was washed with cold 2-propanol and vacuum dried (40° C.) for 48 h. The resulting tan powder weighed 0.248 g (71% yield), mp 174-175.5° C.

Workup

customThe ethanol was evaporated
customto leave a dark brown oil, which
additionwas added drop-wise
temperatureOnce homogeneous, the mixture was cooled to ambient temperature as the walls of the flask
customA tan precipitate formed
filtrationfiltered
washThe filter cake was washed with cold 2-propanol and vacuum
customdried (40° C.) for 48 h

Sources & evidence

ORD record: ord-01595fff22144da2add83e2ab1ed34b8
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979695B2

Reaction notes

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