2-hydroxy-N,N-dimethyl-3-nitrobenzamide → 3-Amino-2-hydroxy-N,N-dimethylbenzamide
Reaction equation
[OH:1][C:2]1[C:12]([N+:13]([O-])=O)=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[H][H]>C(O)C.[Pd]>[NH2:13][C:12]1[C:2]([OH:1])=[C:3]([CH:9]=[CH:10][CH:11]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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%.
Workup
- filtrationThe reaction medium was filtered through celite
- customthe filtrate was evaporated
Sources & evidence
- ORD record
- ord-a2410e0610ae421580cc5ed6912d04bc
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09388149B2
Reaction notes
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