Formic Acid → HCID 15052484, compound

HRID 1074234Notes

Reaction equation

C(O)(C)C.C(O)=O.[CH2:8]([C:10](=[CH:13][CH3:14])[CH:11]=O)[CH3:9].[NH2:15][C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:13]([C:10]1[C:8]([CH3:9])=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N:15][CH:11]=1)[CH3:14]

Participants

Conditions

Temperature: 70 °C

Procedure

Isopropyl alcohol 300 ml and 90% formic acid 12.8 g (0.250 mol) were placed in 500 ml four-neck flask equipped with a reflux condenser. After heating the content to 70° C., a mixture of 2-ethyl-2-butenal 21.6 g (0.22 mol) and ethyl β-amino-β-ethoxycarbonylacrylate 31.1 g (0.166 mol) was added dropwise thereto with air-bubbling and refluxed for 48 hours. To this reaction mixture, conc. hydrochloric acid 10 ml was added dropwise thereto to precipitate remaining ethyl β-amino-β-ethoxy-carbonylacrylate as its hydrochloride form and filtered off at 20° C. Concentration of the filtrate gave 52.2 g of oily substance, which was subjected to silica gel column-chromatography (eluent; ethyl acetate: benzene=1:3) and 10.7 g of 5-ethyl-4-methyl-2,3-diethoxycarbonylpyridine was obtained.

Workup

customequipped with a reflux condenser
additionwas added dropwise
customwith air-bubbling
temperaturerefluxed for 48 hours
additionTo this reaction mixture, conc. hydrochloric acid 10 ml was added dropwise
customto precipitate
filtrationfiltered off at 20° C
customConcentration of the filtrate gave 52.2 g of oily substance, which

Sources & evidence

ORD record: ord-ea0a3442efd742828a70318ba14329ec
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04973695

Reaction notes

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