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

HRID 890131Notes

Reaction equation

HRID 890131 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-f49bd1c91cfa4aafaa2e2487dcea7035
Source dataset
uspto-grants-2006_02
Patent number
US06995178B2

Reaction notes

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