Hydrochloric Acid → 4-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dione

HRID 527129Notes

Reaction equation

HRID 527129 reaction equation
[OH:1][C:2]1([C:16]2[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=2[O:25][CH3:26])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[C:3]1=[O:15].Cl.O>C(O)C.[Fe]>[NH2:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[C:10](=[O:11])[C:2]([OH:1])([C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][C:17]=1[O:25][CH3:26])[C:3]2=[O:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 714769702-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione

Product 1

HCID 714769734-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-2H-inden-1,3-dioneYield 70.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-4-nitro-2H-inden-1,3-dione (52 mg, 1.4 mmol) was completely dissolved in anhydrous ethanol (10 ml). This solution was added with iron (0.59 g, 10.6 mmol), conc. HCl (0.01 ml) and water (1 ml). The reaction mixture was heated for 3 hrs under reflux. After filtration at high temperature to remove iron, the filtrate was concentrated in a vacuum and purified using column chromatography (ethylacetate:hexane=1:2) to afford the title compound (0.32 g, 68%).

Workup

  1. temperatureThe reaction mixture was heated for 3 hrs
  2. temperatureunder reflux
  3. filtrationAfter filtration at high temperature
  4. customto remove iron
  5. concentrationthe filtrate was concentrated in a vacuum
  6. custompurified

Sources & evidence

ORD record
ord-37c9893f9e374e55a443c370c8e6c91a
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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