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Table 1 Synthesis of the Schiff bases 5a–l using NH₄Cl (10 mol%)

From: Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities

Entry	Product^a	R₁, R₂	R₃	Yield^b (%)
1	5a	(C₆H₅)₂	2-OH	92
2	5b	(C₆H₅)₂	4-OCH₃	82
3	5c	(C₆H₅)₂	4-Cl	78
4	5d	(C₆H₅)₂	4-NO₂	75
5	5e	(C₂H₅)₂	2-OH	88
6	5f	(C₂H₅)₂	4-OCH₃	84
7	5g	(C₂H₅)₂	4-Cl	80
8	5h	(C₂H₅)₂	4-NO₂	77
9	5i	1-Piperidinyl	2-OH	90
10	5j	1-Piperidinyl	4-OCH₃	86
11	5k	1-Piperidinyl	4-Cl	84
12	5l	1-Piperidinyl	4-NO₂	74

^aReaction conditions: spiro[indoline-3,4′-pyran]-3′-carbonitrile derivatives 3a–c (10 mmol), aromatic aldehydes 4a–d (10 mmol), and NH₄Cl (10 mol%) in 10 mL ethanol/reflux, 2 h
^bIsolated yields

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