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

HRID 1754011Notes

Reaction equation

HRID 1754011 reaction equation
[NH2:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]#[N:18])=[CH:12][C:3]=1[C:4]([O:6]CCCCC)=O.[CH3:19][NH2:20].C[O-].[Na+]>>[NH2:1][C:2]1[C:15]([CH3:16])=[CH:14][C:13]([C:17]#[N:18])=[CH:12][C:3]=1[C:4]([NH:20][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 10942334Sodium MethoxideHCID 86720218HCID 86720218, compound

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamideYield 70.6%

Procedure

The above-described method (Example 3) was repeated to stir pentyl 2-amino-5-cyano-3-methylbenzoate (1.50 g, mmol) with methylamine (10.8 g, 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 (0.79 g, 70.6% of theory, 96.4 area % LC) was obtained as a brown solid.

Workup

  1. distillationdistilled

Sources & evidence

ORD record
ord-ade4ab555d2d4d968d5968d50769a029
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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