Methylamine → HCID 62173193, compound

HRID 2276910Notes

Reaction equation

HRID 2276910 reaction equation
[CH2:1]([N:3](CC)CC)C.CN.Cl[C:11]1[CH:27]=[CH:26][C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:16])=[CH:13][N:12]=1>CO>[CH3:1][NH:3][C:11]1[CH:27]=[CH:26][C:14]([C:15]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[O:16])=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8471TriethylamineHCID 14832696-chloro-N-(4-methoxyphenyl)nicotinamide

Product 1

HCID 62173193HCID 62173193, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

Methanol (20 mL), triethylamine (1.59 mL, 11.4 mmol) and monomethylamine (2.0 M in MeOH, 19 mL, 38.0 mmol) were added to a pressure tube containing 6-chloro-N-(4-methoxyphenyl)nicotinamide (37, 2.0 g, 7.61 mmol) obtained in step 1. After agitating at 100° C. overnight and then cooling to room temperature, the product was removed by filtration. Removal of the solvent under reduced pressure yielded the target compound 6-(N-monomethylamino)-N-(4-methoxyphenyl)nicotinamide (38, 1.76 g, 90%) without further purification.

Workup

  1. customobtained in step 1
  2. temperaturecooling to room temperature
  3. customthe product was removed by filtration
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5b145deb8da54794be45b23421a6f397
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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