Synthesis of N,N-diallylanilines by the reaction of anilines and allyl bromide in the presence of Mg–Al hydrotalcites at ambient temperature

Figures & data

Table 1. Reaction of aniline and allyl bromide in the presence of different HTs.

			Yield^a of (%)
Entry	Catalyst	Conversion of aniline (%)	Monoallyl aniline	Bisallyl aniline
1	No catalyst	–	17^b	48^b
2	HT5	90	3	87
3	HT3	85	2	83
4	HT2	85	2	83
5	HT5C	87	3	84
6	HT3C	86	2	83
7	HT2C	84	4	80
Note: Reaction conditions: aniline (10 mmol), allyl bromide (20 mmol), catalyst (20 wt.% of aniline), aq. ethanol (50% v/v, 20 mL), temperature RT (30°C).
^aThe yield reported based on GC.
^bIsolated yield, time 90 min.

Table 2. Reaction of aniline and allyl bromide in the presence of different quantities of HT5.

			Yield^a of (%)
Entry	Catalyst quantity (wt.% of aniline)	Conversion of aniline (%)	Monoallyl aniline	Bisallyl aniline
1	20	90	3	87
2	15	85	4	81
3	10	81	3	79
4	5	78	2	76
Notes: Reaction conditions: aniline (10 mmol), allyl bromide (20 mmol), aq. ethanol (50% v/v, 20 mL), temperature RT (30°C). Time 90 min.
^aThe yield reported based on GC.

Table 3. The reaction of aniline and allyl bromide in the presence of HT5.

			Yield of^a (%)
Entry	Run	Conversion of aniline (%)	Monoallyl aniline	Bisallyl aniline
1	1	90	3	87
2	2	89	4	84
3	3	87	3	81
Notes: Reaction conditions: aniline (10 mmol), allyl bromide (20 mmol), HT5 (20 wt.% of aniline), aq. ethanol (50% v/v, 20 mL), temperature RT (30^oC). Time 90 min.
^aThe yield reported based on GC.

Table 4. Reaction of anilines and allyl bromide in the presence of HT5.

Entry	Amine	Product	Time (min)	Yield^c (%)
1^b			90	80
2			45	71
3^b			45	76
4^a			120	44
5^b			90	70
6			100	69
7			110	63
8^b			120	62
9^a			180	10
10			120	78
Note: Reaction conditions: aniline (10 mmol), allyl bromide (22 mmol), HT5 (20 wt.% of aniline), aq. EtOH (50% v/v, 20 mL), temperature RT (30^oC).
^aReaction temperature 80°C.
^bCharacterized using ^1H NMR.
^cIsolated yield.