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

HRID 1754012Notes

Reaction equation

HRID 1754012 reaction equation
[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:3]=1[C:4]([O:6]CCCCCC)=O.[CH3:20][NH2:21].C[O-].[Na+]>>[NH2:1][C:2]1[C:16]([CH3:17])=[CH:15][C:14]([C:18]#[N:19])=[CH:13][C:3]=1[C:4]([NH:21][CH3:20])=[O:6]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 10942334Sodium MethoxideHCID 86720219HCID 86720219, compound

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamideYield 81.1%

Procedure

The above-described method (Example 3) was repeated to stir hexyl 2-amino-5-cyano-3-methylbenzoate (1.40 g, 4.89 mmol) with methylamine (10.8 g, 139 mmol, 40% in methanol) and sodium methoxide (441 mg, 0.12 mmol, 30% in methanol) at room temperature for 18 hours. The entire reaction batch was vacuum distilled and stirred with diisopropyl ether. 2-Amino-5-cyano-N,3-dimethylbenzamide (0.75 g, 75.8% of theory, 93.6 area % LC) was obtained as a brown solid.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-dc6715e0bf894bb4aaf0738a607ea224
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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