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

HRID 1754013Notes

Reaction equation

HRID 1754013 reaction equation
[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]#[N:21])=[CH:15][C:3]=1[C:4]([O:6]CC(CC)CCCC)=O.[CH3:22][NH2:23]>C[O-].[Na+]>[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:16]([C:20]#[N:21])=[CH:15][C:3]=1[C:4]([NH:23][CH3:22])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86720220HCID 86720220, compound

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamideYield 124.9%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideCatalyst

Procedure

The above-described method (Example 3) was repeated to stir 2-ethylhexyl 2-amino-5-cyano-3-methylbenzoate (1.00 g, 3.09 mmol) with methylamine (3.60 g, 46.3 mmol, 40% in methanol) and one drop of sodium methoxide (30% in methanol) at room temperature for 18 hours. The entire reaction batch was vacuum distilled and 2-amino-5-cyano-N,3-dimethylbenzamide (730 mg, 91.4% of theory, 73.1 area % LC) was obtained as a brown solid.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-b5e21a3cfb9e43fbbc89da5880fdf54d
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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