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ChemicalBook CAS DataBase List 3-AMINO-2-HYDROXY-N,N-DIMETHYLBENZAMIDE
464913-11-9

3-AMINO-2-HYDROXY-N,N-DIMETHYLBENZAMIDE synthesis

4synthesis methods
2-hydroxy-N,N-diMethyl-3-nitrobenzaMide

66952-65-6

3-AMINO-2-HYDROXY-N,N-DIMETHYLBENZAMIDE

464913-11-9

Step 7 Synthesis of 3-amino-2-hydroxy-N,N-dimethylbenzamide: 33.5 g of 2-hydroxy-N,N-dimethyl-3-nitrobenzamide was dissolved in 600 mL of ethanol to form a solution. To this solution was added 3.35 g of Pd/C catalyst (suspended in 10 mL of 70 mL of ethanol). The reaction mixture was placed under 2 bar hydrogen atmosphere and the reaction was stirred overnight. The progress of the reaction was monitored by thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) (HPLC retention time t = 0.66 min, molecular ion peak M + 181). Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth pad to remove the catalyst. The filtrate was concentrated under reduced pressure to give 29 g of brown oily solid, 3-amino-2-hydroxy-N,N-dimethylbenzamide, in 100% yield.

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Yield:464913-11-9 100%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethanol; under 1500.15 Torr;

Steps:

1.7 3-Amino-2-hydroxy-N,N-dimethylbenzamide

Step 7
3-Amino-2-hydroxy-N,N-dimethylbenzamide
A solution of 33.5 g of 2-hydroxy-N,N-dimethyl-3-nitrobenzamide in 600 ml of ethanol was added to a suspension of 3.35 g of Pd/C 10% in 70 ml of ethanol.
The reaction medium was stirred under 2 bar of hydrogen overnight. TLC and HPLC control (t=0.66 M+181).
The reaction medium was filtered through celite and the filtrate was evaporated.
29 g of 3-amino-2-hydroxy-N,N-dimethylbenzamide were obtained in the form of an oily brown solid. Yield=100%.

References:

US2014/296254,2014,A1 Location in patent:Paragraph 0102