US 12,466,794 B1
Pyrrole synthesis method using juice catalyst
M. Amin Mir, Dhahran (SA); Syed M. Hasnain, Dhahran (SA); and K. Andrews, Dhahran (SA)
Assigned to PRINCE MOHAMMAD BIN FAHD UNIVERSITY, Dhahran (SA)
Filed by PRINCE MOHAMMAD BIN FAHD UNIVERSITY, Dhahran (SA)
Filed on Apr. 23, 2025, as Appl. No. 19/187,847.
Int. Cl. C07D 207/323 (2006.01); B01J 31/04 (2006.01); C07D 207/325 (2006.01)
CPC C07D 207/323 (2013.01) [B01J 31/04 (2013.01); C07D 207/325 (2013.01)] 9 Claims
 
1. A method of making an N-substituted pyrrole, comprising:
reacting an amine of formula (5),

OG Complex Work Unit Chemistry
with a compound of formula (6),

OG Complex Work Unit Chemistry
in the presence of a juice catalyst from a fruit of a plant in the genus Malus, to form a compound of formula (4),

OG Complex Work Unit Chemistry
wherein R4, R5, R6, and R7 are each independently a hydrogen, an optionally substituted alkyl, or an optionally substituted aryl;
wherein R8 is an aryl group;
wherein greater than 70 mol % of the total number of moles of organic acid present in the juice are malic acid; and
wherein the reacting is performed at 50 to 75° C. for 5 to 10 hours.