Hydrochloric Acid → 2-(3-thienyl)benzaldehyde

To a solution of Compound 2b (1.98 mmol) in chloroform (5 mL) was added pyridine (9.88 mmol) and the reaction mixture heated at reflux for 1 hour under nitrogen. The solvent was removed in vacuo and the residue triturated with diethyl ether to give a white solid. The solid was dissolved in 95% aqueous ethanol (10 mL ) and N,N-dimethyl-4-nitrosoaniline (1.98 mmol) was added with stirring followed by the addition of sodium hydroxide (4.0 mmol) in water (3 mL). The reaction mixture was stirred for 16 hours at ambient temperature and then 6N hydrochloric acid (3 mL) was added. After 30 minutes, the solvent was removed in vacuo and the residue was diluted with water (10 mL) and extracted with diethyl ether (2×30 mL). The combined organic phases were washed with saturated aqueous sodium bicarbonate, brine and the solvent removed in vacuo to give crude Compound 2c as an oil.

1. temperaturethe reaction mixture heated
2. temperatureat reflux for 1 hour under nitrogen
3. customThe solvent was removed in vacuo
4. customthe residue triturated with diethyl ether
5. customto give a white solid
6. stirringThe reaction mixture was stirred for 16 hours at ambient temperature
7. customthe solvent was removed in vacuo
8. additionthe residue was diluted with water (10 mL)
9. extractionextracted with diethyl ether (2×30 mL)
10. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate, brine
11. customthe solvent removed in vacuo

ORD record

ord-c307eb18a9c64f08bbb10f86adf65512

Source dataset

uspto-grants-1986_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04599341