N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide → 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide

HRID 883040Notes

Reaction equation

HRID 883040 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:22])[C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([N+:19]([O-])=O)[CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:19][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][C:15]=1[CH3:18])[C:11]([NH:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=1)=[O:22]

Participants

4

Reactant 1

HCID 26177932N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide

Product 1

HCID 251022283-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To N-(3-isopropyl-phenyl)-4-methyl-3-nitro-benzamide (3.0 g, 0.010 mol) dissolved in EtOAc (60 mL) in a 100 mL RBF was added Pd/C (10%, 250 mg). The flask was capped with a rubber septum and flushed with H2 gas through a balloon/needle. Positive H2 pressure was applied through the balloon/needle and reaction was stirred vigorously at room temperature for 3 days. TLC indicated clean conversion of starting material. The reaction was filtered through a pad of sand/celite. After concentration, the mixture was purified by silica gel chromatography to afford a light orange oil. Trituration with a mixture of hexanes and EtOAc afforded 3-amino-N-(3-isopropyl-phenyl)-4-methyl-benzamide as an off-white solid. MS m/z 269=[M+H]+. Calc'd for C17H20N2O: 268.36.

Workup

  1. customThe flask was capped with a rubber septum
  2. customflushed with H2 gas through a balloon/needle
  3. customPositive H2 pressure was applied through the balloon/needle and reaction
  4. filtrationThe reaction was filtered through a pad of sand/celite
  5. concentrationAfter concentration
  6. customthe mixture was purified by silica gel chromatography
  7. customto afford a light orange oil

Sources & evidence

ORD record
ord-3c8c164bd9484d2f98b8970f6add4833
Source dataset
uspto-grants-2012_08
Patent number
US08236823B2

Reaction notes

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