Table 1.

Synthesis of carbonitrile 4–6 and their corresponding methyl carbimidates 7–9.

Amine (R-NH2)	Compound	Yield (%) a	Time (min)	Compound	Yield (%) a
4-methoxyaniline	4a	99	2	7a	82
3,4-(methylenedioxy)aniline	4b	95	45	7b	92
1,4-benzodioxan-6-amine	4c	33	15	7c	80
2,3-dihydro-1-benzofuran-5-amine	4d	95	5	7d	66
3,4-dimethoxyaniline	4e	74	15	7e	89
2,4-dimethoxyaniline	4f	59	2	7f	71
3,5-dimethoxyaniline	4g	98	7	7g	58
3-nitro-4-methoxyaniline	4h	61	20	7h	59
4-aminophenol	4i	80	5	7i	81
5-amino-2-methoxyphenol	4j	54	5	7j	99
4-amino-2-nitrophenol	4k	60	15	7k	34
3,4,5-trimethoxyaniline	4l	85	5	7l	94
4-chloroaniline	5a	89	10	8a	62
3-chloroaniline	5b	74	20	8b	78
2,4-dichloroaniline	5c	32	50	8c	81
3,4-dichloroaniline	5d	42	20	8d	45
4-fluoroaniline	5e	92	5	8e	77
4-bromo-2-fluoroaniline	5f	78	30	8f	94
3-chloro-4-fluoroaniline	5g	82	10	8g	98
4-chloro-2-fluoroaniline	5h	56	20	8h	58
2-fluoro-4-methoxyaniline	5i	85	5	8i	82
4-amino-2-fluorophenol	5j	58	10	8j	70
2,4-difluoroaniline	5k	68	15	8k	71
4-aminobenzotrifluoride	5l	61	15	8l	53
aniline	6a	67	5	9a	52
4-toluidine	6b	64	2	9b	88
4- tert-butylaniline	6c	99	5	9c	69
3-ethynylaniline	6d	84	15	9d	68
4-aminobenzonitrile	6e	36	20	9e	52
3-aminobenzonitrile	6f	80	10	9f	33
6-aminobenzimidazole	6g	98	10	9g	57
N,N-dimethyl-p-phenylene-diamine	6h	25	15	9h	94
4-(pyrrolidin-1-yl)aniline	6i	48	5	9i	75

^a Isolated yields.