Water → 2-Amino-5-Chloro-N,3-Dimethylbenzamide

HRID 490974Notes

Reaction equation

HRID 490974 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:3]=1[C:4](OC)=[O:5].[CH3:14][NH2:15].O>C(#N)C.C(O)CO>[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]([Cl:13])=[CH:8][C:3]=1[C:4]([NH:15][CH3:14])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 12744623Methyl 2-amino-5-chloro-3-methylbenzenecarboxylate

Product 1

HCID 250682512-Amino-5-Chloro-N,3-DimethylbenzamideYield 85.5%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of methyl 2-amino-5-chloro-3-methylbenzoate (i.e. the product of Example 2) (4.03 g, 20.2 mmol) in acetonitrile (12.4 g) was added a solution of methylamine (3.1 g, 0.10 mol) in ethylene glycol (12.4 g). The mixture was heated at 60° C. for 23 h, and then cooled to room temperature. Water (25 mL) was added dropwise, and the resulting slurry was cooled to 5° C. and stirred for 10 minutes at this temperature. The mixture was filtered, and the solids were washed with water (3×10 mL), and dried under nitrogen to afford the title compound as white needles, 3.43 g (85.5% yield).

Workup

  1. temperaturecooled to room temperature
  2. temperaturethe resulting slurry was cooled to 5° C.
  3. filtrationThe mixture was filtered
  4. washthe solids were washed with water (3×10 mL)
  5. customdried under nitrogen

Sources & evidence

ORD record
ord-ca9a841fc1b94c14a6523cd1297a8bb9
Source dataset
uspto-grants-2009_05
Patent number
US07528260B2

Reaction notes

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