HCID 59442723, compound → HCID 59442706, compound

HRID 388248Notes

Reaction equation

HRID 388248 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[NH:14][CH:15]([CH3:17])[CH3:16])([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([O:4][C:5]1[C:6]([NH:14][CH:15]([CH3:17])[CH3:16])=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59442723HCID 59442723, compound

Product 1

HCID 59442706HCID 59442706, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (385 mg, 1.62 mmol, 1 equiv) in ethanol (3 mL) was charged with 10% Pd/C (50% water, 253 mg, 0.162 mmol, 0.10 equiv) and air was evacuated with vacuum. The vacuum was replaced with a balloon filled with hydrogen gas, and the reaction was allowed to stir for 2 hours. The catalyst was filtered off using a pad of celite and rinsed with ethanol. The filtrate was concentrated, and the crude product was purified by flash chromatography and eluted with hexane:EtOAc=100:0 to 50:50 using 5% EtOAc increments to give 6-isopropoxy-N1-isopropylbenzene-1,3-diamine 31 (263 mg, 78%) as a solid.

Workup

  1. customwas evacuated with vacuum
  2. additionfilled with hydrogen gas
  3. filtrationThe catalyst was filtered off
  4. washrinsed with ethanol
  5. concentrationThe filtrate was concentrated
  6. customthe crude product was purified by flash chromatography
  7. washeluted with hexane

Sources & evidence

ORD record
ord-f09141e064a34dea94f0628ad6c40db4
Source dataset
uspto-grants-2013_02
Patent number
US08377924B2

Reaction notes

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