HCID 59442751, compound → HCID 59442721, compound

HRID 388249Notes

Reaction equation

HRID 388249 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[N:14]([CH:16]([CH3:18])[CH3:17])[CH3:15])([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:1]([O:4][C:5]1[C:6]([N:14]([CH:16]([CH3:18])[CH3:17])[CH3:15])=[CH:7][C:8]([NH2:11])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 59442751HCID 59442751, compound

Product 1

HCID 59442721HCID 59442721, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-isopropoxy-N-isopropyl-N-methyl-5-nitrobenzenamine 3 (300 mg, 1.19 mmol, 1 equiv) in ethanol (3 mL) was charged with 10% Pd/C (50% water, 253 mg, 0.119 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 to give 6-isopropoxy-N1-isopropyl-N1-methylbenzene-1,3-diamine 5 (264 mg, 100%) as a solid which was used in the next step without further purification.

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

Sources & evidence

ORD record
ord-815fa793e343470cb038e7bc7e7de806
Source dataset
uspto-grants-2013_02
Patent number
US08377924B2

Reaction notes

Loading…