Hydroxyamine hydrochloride → 1-Ethyl-1H-pyrrole-2-carbonitrile

1-Ethylpyrrole-2-carbaldehyde (cf. J. Chem. Soc. (C), 2563, 1970) (7.4 g, 60 mmole), hydroxylamine hydrochloride (4.8 g, 69 mmole) sodium acetate trihydrate (9.4 g, 69 mmole) and water (30 ml) are mixed, and the mixture is stirred at room temperature for 20 minutes and then allowed to stand in a cooled place overnight. The precipitated oxime compound is taken by filtration and dried. The oxime compound is refluxed in acetic anhydride (25 ml) for 20 minutes and then allowed to cool until room temperature. The reaction mixture is added to ice water, and the mixture is stirred for 2 hours and neutralized with sodium carbonate and extracted with ether twice. The ether layer is dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The resulting residue is distilled under reduced pressure to give 1-ethylpyrrole-2-carbonitrile (5.25 g, yield: 73%).

1. customto stand in a cooled place overnight
2. filtrationThe precipitated oxime compound is taken by filtration
3. customdried
4. temperatureThe oxime compound is refluxed in acetic anhydride (25 ml) for 20 minutes
5. temperatureto cool until room temperature
6. additionThe reaction mixture is added to ice water
7. stirringthe mixture is stirred for 2 hours
8. extractionextracted with ether twice
9. dry with materialThe ether layer is dried over anhydrous magnesium sulfate
10. distillationthe solvent is distilled off under reduced pressure
11. distillationThe resulting residue is distilled under reduced pressure

ORD record

ord-dfdde23f9631427a91d71993e84455fe

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04659726