Hydrochloric Acid → HCID 43299111, compound

Temperature

90 °C

Iron powder (330 mg) and conc. hydrochloric acid (0.3 ml) were added to a solution of 1-(3-hydroxypropylthio)-4-nitrobenzene (Method 82; 1 g, 4.69 mmol) in ethanol (6 ml) and water (3 ml). The mixture was stirred and heated at 90° C. for 3 hours, further iron powder (300 mg) and conc. HCl (0.2 ml) were added and heating continued for a further 2 hours. The volatiles were removed by evaporation and water (20 ml) added to the residue. The mixture was acidified to pH 1 with 2M hydrochloric acid, filtered through diatomaceous earth, and the filtrate washed with EtOAc (2×25 ml). The aqueous layer was basified to pH11 with conc. aqueous sodium hydroxide solution and extracted with EtOAc (2×25 ml). The extracts were combined, washed with brine (15 ml), dried and evaporated under reduced pressure to give the title compound (900 mg, 100%). m/z 184.

1. temperatureheating
2. customThe volatiles were removed by evaporation and water (20 ml)
3. additionadded to the residue
4. filtrationfiltered through diatomaceous earth
5. washthe filtrate washed with EtOAc (2×25 ml)
6. extractionextracted with EtOAc (2×25 ml)
7. washwashed with brine (15 ml)
8. customdried
9. customevaporated under reduced pressure

ORD record

ord-57c6bb40aa0a40d1b14a6a099d794966

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465728B2