2-hydroxy-N,N-dimethyl-3-nitrobenzamide → 3-Amino-2-hydroxy-N,N-dimethylbenzamide

HRID 1528151Notes

Reaction equation

HRID 1528151 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

HCID 113678032-hydroxy-N,N-dimethyl-3-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 160984833-Amino-2-hydroxy-N,N-dimethylbenzamideYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 33.5 g of 2-hydroxy-N,N-dimethyl-3-nitrobenzamide in 600 ml of ethanol were 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

  1. filtrationThe reaction medium was filtered through celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1f305bcd9200474aaa6f7fab72f24f46
Source dataset
uspto-grants-2015_07
Patent number
US09090596B2

Reaction notes

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