2,2-Dioxo-1,3-dihydrobenzo[c]thiophene-5yl amine

Synthesis

General procedure: 5-nitro-1,3-dihydrobenzo[c]thiophene 2,2-dioxide (Compound 86.4, 0.12 g, 0.56 mmol, 1.0 eq.) was added to a suspension of 10% Pd/C (0.03 g) in methanol (3.0 mL). The suspension was purged with hydrogen (H2) gas for 1 hour. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure to afford 5-amino-1,3-dihydrobenzo[c]thiophene 2,2-dioxide (Compound 86.5, 0.08 g, 77.5% yield). Mass spectrum (electrospray ionization): m/z 184.1 [M + H]+.

References

[1] Russian Chemical Bulletin, 2005, vol. 54, # 2, p. 437 - 440
[2] Patent: US2016/251376, 2016, A1. Location in patent: Paragraph 1028; 1035; 1036
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 8, p. 2399 - 2406