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

HRID 1754010Notes

Reaction equation

HRID 1754010 reaction equation
[CH3:1][NH2:2].[NH2:3][C:4]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:5]=1[C:6]([O:8]CC)=O.C[O-].[Na+].[OH-].[Na+]>CO>[NH2:3][C:4]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]#[N:17])=[CH:11][C:5]=1[C:6]([NH:2][CH3:1])=[O:8]

Participants

6

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 25156989HCID 25156989, compound

Product 1

HCID 251572822-Amino-5-cyano-N,3-dimethylbenzamideYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methylamine (117 g, 3.77 mol) is introduced into a solution of ethyl 2-amino-5-cyano-3-methylbenzoate (50 g, 0.251 mol) in methanol (175 mL), sodium methoxide (1.13 g, 30% strength in methanol, 6.28 mmol) is added and the reaction mixture is stirred overnight at room temperature. Thereafter, 100 ml of 22% strength NaOH are added and the batch is cooled down to 10° C. The suspension obtained is filtered and the solid obtained is washed once with 1:1 methanol:water and then with 50 mL of water. The solid is dried at 50° C. in a vacuum drying cabinet. 2-Amino-5-cyano-N,3-dimethylbenzamide is isolated as a slightly beige solid. Yield: 80.3% of theory, purity: 94.9% quantitative LC, 73 ppm Cu).

Workup

  1. additionis added
  2. temperaturethe batch is cooled down to 10° C
  3. customThe suspension obtained
  4. filtrationis filtered
  5. customthe solid obtained
  6. washis washed once with 1:1 methanol
  7. customThe solid is dried at 50° C. in a vacuum
  8. customdrying cabinet

Sources & evidence

ORD record
ord-6a2c66001ead48ef97ee76ddbc926ccd
Source dataset
uspto-grants-2015_10
Patent number
US09169198B2

Reaction notes

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