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

HRID 2243473Notes

Reaction equation

HRID 2243473 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]>[Pd].C(O)C>[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 D (1.70 g, 7.6 mmol) was hydrogenated over 5% palladium on carbon in 40 mL of ethanol at 345 kPa (50 psi). When the uptake of hydrogen ceased the reaction was filtered through Celite® filter agent 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. filtrationfilter agent
  3. washthe Celite® was washed with ether
  4. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-15a7b747b2b24f26826f7f2c832f21b7
Source dataset
uspto-grants-2010_03
Patent number
US07674936B2

Reaction notes

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