Efficient Synthesis of 1-Amidoalkyl-2-Naphthols by One-Pot, Three-Component Reaction under Solvent-Free Conditions

Table 1

Synthesis of 1-aminomethyl 2-naphthols.

Entry	R	R^′	Method A		Method B		m.p. (^°C)	[Ref.]
			Time (min)	Yield (%)	Time (h)	Yield (%)
1	H	CH3	3	85	1.5	76	240-241	[8]
2	4-NO2	CH3	3	93	2	79	229–232	[8]
3	4-F	CH3	10	82	1.5	68	224–226	[8]
4	2-NO2	CH3	15	95	1	83	217–220	[14]
5	2,4-Cl2	CH3	12	93	3	88	212–215	[8]
6	2,6-Cl2	CH3	4	95	3	79	228–230	[14]
7	2-Cl	CH3	11	88	1.5	78	208-209	[14]
8	2-Cl-6-F	CH3	4	91	1	90	225–227	[14]
9	4-Br	CH3	4	95	2	83	235–238	[15]
10	3-NO2	CH3	3	95	1.5	89	241–243	[12]
11	4-Cl	CH3	7	88	2	88	235–238	[14]
12	4-Me	CH3	10	89	1.5	78	219–221	[16]
13	3-OMe	CH3	2	87	2.5	70	236–238	[8]
14	H	CH2=CH	1	98	1.5	90	249-250	[10]
15	3-NO2	CH2=CH	1	97	2	96	257–259	[10]
16	4-NO2	CH2=CH	10	85	1.5	89	218–220	[18]
17	H	C6H5	1	99	1	85	234–236	[15]
18	4-NO2	C6H5	7	93	1	90	238–240	[17]
19	3-NO2	C6H5	21	99	1	90	241–243	[14]
20	2-NO2	C6H5	1	91	1	90	266-267	[14]
21	3-OMe	C6H5	1	99	1	80	217–220	[11]
22	2,4-Cl2	C6H5	1	98	1	85	262-263	[14]
23	2-Cl	C6H5	1	97	1	85	285-286	[14]
24	Propionaldehyde	CH3	67	Trace	—	—	—