Methylamine → 2-Amino-5-cyano-N,3-dimethylbenzamide

HRID 1754014Notes

Reaction equation

HRID 1754014 reaction equation
[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:15])=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[CH3:16][NH2:17].C[O-].[Na+]>>[NH2:1][C:2]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]#[N:15])=[CH:9][C:3]=1[C:4]([NH:17][CH3:16])=[O:6]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 10942334Sodium MethoxideHCID 25156989HCID 25156989, compound

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamideYield 96.9%

Procedure

The above-described method (Example 3) was repeated to stir ethyl 2-amino-5-cyano-3-methylbenzoate (0.50 g, 2.40 mmol) with methylamine (3.73 g, 48 mmol, 40% in methanol) and sodium methoxide (22 mg, 30% in methanol) at room temperature for 18 hours. The entire reaction batch was vacuum distilled and 2-amino-5-cyano-N,3-dimethylbenzamide (0.44 g, 95.9% of theory, 99.0 area % LC) was obtained as a pale brown solid.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-c2a58dffb30346abb73f015518bf15f4
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

Loading…