Hydrochloric Acid → HCID 136346820, compound

Participants

Reaction Conditions

Reaction Steps

1,3-Dihydro-pyrrolo[3,2-f]quinoline-2-one (552 mg, 3.00 mmol) was combined with 855 mg (3.05 mmol) of 3,5-dibromo-4-hydroxybenzaldehyde (TCl Chemicals) in 6 mL of glacial acetic acid with 1 mL of concentrated hydrochloric acid. The reaction was stirred at 115° C. for 8 hr, cooled and filtered, washing with ethyl acetate, to give 1.32 g of 1-(3,5-Dibromo-4-hydroxy-benzylidene)-1,3-dihydro-pyrrolo[3,2-f]quinolin-2-one hydrochloride as a brown solid which consisted of a 9/1 mixture of Z/E isomers. Mass spectrum (negative ion chemical ionization): m/z=443 (40%), 445 (100%), 447 (40%). 1H NMR (DMSO-d6): δ7.69 (d, J=8.8 Hz, 1H); 7.93 (dd, J=8.7, 4.9 Hz, 1H); 8.24 (d, J=8.8 Hz, 1H); 8.27 (s, 1H); 8.80 (s, 1H); 9.04 (d, J=4.7 Hz, 1H); 9.51 (d, J=8.6 Hz, 1H); 11.3 (s, 1H).

Provenance & Evidence