Benzene, 1-(1,1-dimethylethoxy)-2-nitro- → HCID 14763309, compound

HRID 1747769Notes

Reaction equation

HRID 1747769 reaction equation
[C:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 10997909Benzene, 1-(1,1-dimethylethoxy)-2-nitro-

Product 1

HCID 14763309HCID 14763309, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-tert-butoxy-2-nitrobenzene (Journal of Organic Chemistry, 1998, 63, 25, 9495-9496.) (15.0 g) in methanol (300 mL) was added 10% palladium on carbon (1.67 g), and the mixture was stirred at room temperature for 30 hr under a hydrogen atmosphere. Palladium on carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (12.4 g).

Workup

  1. customPalladium on carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-51075b9c336f441a9ed19910bd98ade2
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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