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Table 2 The effect of reaction condition on the synthesis of 5a

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	Solvent^a	Catalyst^b	Yield^c (%)
1	AcOH	–	47
2	MeOH	–	40
3	EtOH	–	44
4	DMF	AcOH	52
5	EtOH	AcOH	61
6	EtOH	Et₃N	71
7	EtOH	Piperidine	71
8	Dioxane	NH₄Cl	73
9	DMF	NH₄Cl	75
10	MeOH	NH₄Cl	87
11	EtOH	NH₄Cl	92

The reaction was carried out with ethyl 2′-amino-3′-cyano-1-((diphenylamino)methyl)-6′-methyl-2-oxospiro[indoline-3,4′-pyran]-5′-carboxylate (3a) (10 mmol) and 2-hydroxybenzaldehydes (4a) (10 mmol)
^a10 mL solvent/reflux, 2 h
^b10 mol%
^cIsolated yields

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