HCID 68724254, compound → HCID 68726057, compound

To the refluxing solution of 7-chloro-5-nitrobenzo[b]thiophen obtained in step 4 (4.4 g, 20 mmol) in 5% acetic acid (300 ml) and ethyl acetate (300 ml) was added portion wise iron powder (6 g, 100 mmol) and the mixture was refluxed for 4 h. The reaction mixture was cooled, filtered through celite and washed with ethyl acetate. The layers were separated and the aqueous layer was extracted in ethyl acetate. The combined organic extracts were washed with water, dried and concentrated. The residue was purified by column chromatography (silica gel, hexane:ethyl acetate/4:1) to give 7-chloro-benzo[b]thiophen-5-ylamine, 2 g. MS m/z 183 (M+).

1. temperaturethe mixture was refluxed for 4 h
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered through celite
4. washwashed with ethyl acetate
5. customThe layers were separated
6. extractionthe aqueous layer was extracted in ethyl acetate
7. washThe combined organic extracts were washed with water
8. customdried
9. concentrationconcentrated
10. customThe residue was purified by column chromatography (silica gel, hexane:ethyl acetate/4:1)

ORD record

ord-98da0199bfe34498bf4dc29fa0b5e9bd

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507509B2