4-Neopentyl-2-nitroaniline → 4-Neopentylbenzene-1,2-diamine

HRID 1424222Notes

Reaction equation

HRID 1424222 reaction equation
[CH2:1]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1)[C:2]([CH3:5])([CH3:4])[CH3:3]>CO.[Pd]>[CH2:1]([C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 858027694-Neopentyl-2-nitroaniline

Product 1

HCID 866990534-Neopentylbenzene-1,2-diamineYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-neopentyl-2-nitroaniline (Preparation 88, 5.23 g, 25.1 mmol) in methanol (50 mL) was added 10% palladium on carbon (800 mg, 8 mmol) and hydrogenated at 40 psi for 3.5 hours. The mixture was filtered through celite and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with a 0-10% methanol/methylene chloride gradient to provide the title compound (2.95 g, 66%) as a purple solid.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified
  4. washeluting with a 0-10% methanol/methylene chloride gradient

Sources & evidence

ORD record
ord-2de7fd6c5c904fc6839d036e05e6df9d
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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