Acetic Anhydride → 3-(4-Chloro-pyridin-2-yl)-thiophene-2-carbonitrile

HRID 910699Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[CH:13]=O)[CH:3]=1.Cl.[NH2:16]O.C(OC(=O)C)(=O)C>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:12]=[CH:11][S:10][C:9]=2[C:13]#[N:16])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-(4-chloro-pyridin-2-yl)-thiophene-2-carbaldehyde (103 mg, 0.46 mmol) and hydroxylamine hydrochloride (70 mg, 1 mmol) in pyridine (1 mL) was heated at 80° C. for 30 minutes. Acetic anhydride (0.8 mL) was added and the resulting mixture was heated at the temperature for another 3 hours. Ice water was added, the water solution was extracted with EtOAc and organic layer was concentrated. The resulting residue was purified by silica gel column to yield 3-(4-chloro-pyridin-2-yl)-thiophene-2-carbonitrile.

Workup

temperaturethe resulting mixture was heated at the temperature for another 3 hours
extractionthe water solution was extracted with EtOAc and organic layer
concentrationwas concentrated
customThe resulting residue was purified by silica gel column

Sources & evidence

ORD record: ord-74df5ebe0730433ca740f81e9db82d15
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022209B2

Reaction notes

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