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

HRID 2059999Notes

Reaction equation

HRID 2059999 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:25])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[N+:22]([O-])=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])[CH3:3]>C(OCC)(=O)C.[Pd]>[CH3:14][C:11]([O:10][C:8](=[O:9])[CH:7]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[NH2:22])[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:25])([CH3:12])[CH3:13]

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-646bac1bb66a4ccca3f1c4e6dc653394
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

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