Table 3.

The prepared (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones 6aa–ef with a secondary amino group (R² and R³: H).

entry	product	R1	R4	n1a–e/n2a–d (mmol)	m1a–e (mg)	m3a–i (mg)	yield 6aa–ee (mg)/(%)	mp (°C)
1	6aa	H	C6H5	3.3/3	700	640	721/(77%)	322.5–325
2	6ab	H	4-CH3O-C6H4	3.3/3	700	682	827/(88%, 82%a)	271–273
3	6ac	H	4-Cl-C6H4	3.3/3	700	743	503/(48%)	286.5–288
4	6ad	H	4-CF3-C6H4	3.3/3	700	844	488/(43%)	282–284
5	6ae	H	4-NO2-C6H4	3.3/3	700	775	339/(32%)	281–283.5
6	6af	H	CH3	2.75/2.5	556	378	475/(76%)	256–258
7	6ag	H	CH3(CH2)4	3.3/3	700	622	652/(71%)	214–216
8	6ah	H	C6H5CH2	3.3/3	700	724	696/(71%)	231–234
9	6ai	H	cyclo-C6H11	3.3/3	700	658	613/(64%)	343–346
10	6ba	5-CH3	C6H5	3.15/3	712	640	674/(69%)	258–261
11	6ca	5-Cl	C6H5	1.31/1.25	324	267	380/(89%, 68%b)	242–243
12	6da	6-Cl	C6H5	3.15/3	776	640	749/(72%)	319–322
13	6ea	5-NO2	C6H5	2.1/2	540	427	529/(74%)	267–269
14	6bf	5-CH3	CH3	3.15/3	712	454	521/(66%)	255–257.5
15	6cf	5-Cl	CH3	3.15/3	776	454	605/(71%)	256–258
16	6df	6-Cl	CH3	3.15/3	776	454	719/(84%)	274–276.5
17	6ef	5-NO2	CH3	3.15/3	810	454	656/(74%)	332.5–335

^aPrepared from 2-(phenylethynyl)phenylisocyanate (see reference [23]); ^bthe E-isomer prepared from 3-bromo-3-(bromo(phenyl)methyl)-5-chlorooxindole (see reference [27]).