Complex sentence: At the Constitutional Convention at Hillsborough, North Carolina in 1788, he had similar reservations about the Constitution to other Anti-Federalists at the meeting, and asked if he could challenge some of the clauses.
Split into simpler sentences: At the Constitutional Convention held at Hillsborough, North Carolina in 1788, he had reservations about the Constitution--as did other Anti-Federalists at the meeting. Rutherford asked if he could challenge some of the clauses.