3-isopropoxynitrobenzene → 3-(Propan-2-yloxy)aniline

HRID 1614202Notes

Reaction equation

HRID 1614202 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([N+:11]([O-])=O)[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[H][H]>C(O)C.O=[Pt]=O>[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 121238953-isopropoxynitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 5732203-(Propan-2-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-isopropoxynitrobenzene (8.5 g, 50 mmol) and PtO2 (0.3 g) in 200 ml of ethanol was shaken under 40 psi hydrogen at room temperature for 1.5 hours. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo to provide 7.08 g of light oil (3-isopropoxyaniline). The oil was added to isatoic anhydride (7.35 g, 45 mmol) along with 15 ml of ethyl acetate. The mixture was heated in a 90° oil bath under nitrogen for two hours. The product crystallized from the reaction mixture upon the addition of hexanes. Filtration of the reaction mixture provided 10.19 g (83%) of 2-amino-N-(3-isopropoxyphenyl)benzamide as a white solid.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8c2582ad33f8479fa6f75a5cc080b400
Source dataset
uspto-grants-1993_03
Patent number
US05196427

Reaction notes

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