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

HRID 1754015Notes

Reaction equation

HRID 1754015 reaction equation
[NH2:1][C:2]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:3]=1[C:4]([O:6]CCOC)=O.[CH3:18][NH2:19]>C[O-].[Na+]>[NH2:1][C:2]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:3]=1[C:4]([NH:19][CH3:18])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86720221HCID 86720221, compound

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideCatalyst

Procedure

The above-described method (Example 3) was repeated to stir 2-methoxyethyl 2-amino-5-cyano-3-methylbenzoate (200 mg, 0.81 mmol) with methylamine (5.40 g, 69.5 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 following purification by column chromatography, 2-amino-5-cyano-N,3-dimethylbenzamide (150 mg, 95.0% of theory, 97.8 area % LC) was obtained as a pale brown solid.

Workup

  1. distillationdistilled
  2. custompurification by column chromatography

Sources & evidence

ORD record
ord-3a1a58105a3b40fea265715cabe0e86f
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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