Di-tert-butyl 2-(4-methyl-2-nitrophenyl)malonate → Di-tert-butyl 2-(2-amino-4-methylphenyl)malonate

HRID 1968954Notes

Reaction equation

HRID 1968954 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:4]([N+:23]([O-])=O)[CH:3]=1>C(OCC)(=O)C.[Pd]>[NH2:23][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[CH:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17]

Participants

4

Reactant 1

HCID 57856684Di-tert-butyl 2-(4-methyl-2-nitrophenyl)malonate

Product 1

HCID 57856669Di-tert-butyl 2-(2-amino-4-methylphenyl)malonateYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of bis(1,1-dimethylethyl) (4-methyl-2-nitrophenyl)propanedioate (D38, 660 mg, 1.88 mmol) in ethyl acetate (25 mL) was treated with 10% Pd/C (0.5 g) and shaken under hydrogen at atmospheric pressure and room temperature for 20 hours. The mixture was filtered through Kieselguhr and the filtrate concentrated under vacuum to afford the title compound as a colourless oil (606 mg, 100%).

Workup

  1. filtrationThe mixture was filtered through Kieselguhr
  2. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-4d8e4267ffae47f8a294cac673210149
Source dataset
uspto-grants-2013_04
Patent number
US08426443B2

Reaction notes

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