3-methyl-N-(1-methylethyl)-2-nitrobenzamide → 2-amino-3-methyl-N-(1-methylethyl)benzamide

HRID 352446Notes

Reaction equation

HRID 352446 reaction equation
[CH3:1][C:2]1[C:3]([N+:14]([O-])=O)=[C:4]([CH:11]=[CH:12][CH:13]=1)[C:5]([NH:7][CH:8]([CH3:10])[CH3:9])=[O:6].[H][H]>C(O)C.[Pd]>[NH2:14][C:3]1[C:2]([CH3:1])=[CH:13][CH:12]=[CH:11][C:4]=1[C:5]([NH:7][CH:8]([CH3:10])[CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 8902723-methyl-N-(1-methylethyl)-2-nitrobenzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 167760932-amino-3-methyl-N-(1-methylethyl)benzamideYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The 2-nitrobenzamide of Step A (1.70 g, 7.6 mmol) was hydrogenated over 5% Pd/C in 40 mL of ethanol at 50 psi. When the uptake of hydrogen ceased the reaction was filtered through celite and the celite was washed with ether. The filtrate was evaporated under reduced pressure to afford 1.41 g of the title compound as a solid melting at 149-151° C.

Workup

  1. filtrationwas filtered through celite
  2. washthe celite was washed with ether
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e82d6937c51b4cf6911df1f6dd601185
Source dataset
uspto-grants-2004_06
Patent number
US06747047B2

Reaction notes

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