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

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3-Amino-2-hydroxy-N,N-dimethylbenzamide Basic information
Product Name:3-Amino-2-hydroxy-N,N-dimethylbenzamide
Synonyms:3-aMino-N,N-diMethylsalicylaMide;Benzamide, 3-amino-2-hydroxy-N,N-dimethyl-;3-Amino-2-hydroxy-N,N-dimethylformamide;3-Amino-2-hydroxy-N,N-dimethylbenzamide
CAS:464913-11-9
MF:C9H12N2O2
MW:180.2
EINECS:
Product Categories:
Mol File:464913-11-9.mol
3-Amino-2-hydroxy-N,N-dimethylbenzamide Structure
3-Amino-2-hydroxy-N,N-dimethylbenzamide Chemical Properties
Boiling point 374.5±37.0 °C(Predicted)
density 1.239±0.06 g/cm3(Predicted)
storage temp. Keep in dark place,Inert atmosphere,Room temperature
pka8.07±0.35(Predicted)
Safety Information
MSDS Information
3-Amino-2-hydroxy-N,N-dimethylbenzamide Usage And Synthesis
Uses3-Amino-2-hydroxy-N,N-dimethylbenzamide is a useful research chemical compound used int he synthesis of 3,4-diaminocyclobut-3-ene-1,2-dione CXCR2 antagonists.
Synthesis
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.

References[1] Patent: US2014/296254, 2014, A1. Location in patent: Paragraph 0102
[2] Patent: US2014/309208, 2014, A1. Location in patent: Paragraph 0110; 0115
[3] Patent: US2015/87675, 2015, A1. Location in patent: Paragraph 0152
[4] Patent: WO2004/33440, 2004, A1. Location in patent: Page 166
[5] Patent: US2004/147559, 2004, A1. Location in patent: Page 80
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