Hydrochloric Acid → N-(5-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

HRID 527133Notes

Reaction equation

HRID 527133 reaction equation
[OH:1][C:2]1([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][C:21]=2[O:29][CH3:30])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:16]([O-])=O)[C:8]=2[NH:12][C:13](=[O:15])[CH3:14])[C:3]1=[O:19].Cl.O>C(O)C.[Fe]>[NH2:16][C:7]1[C:8]([NH:12][C:13](=[O:15])[CH3:14])=[C:9]2[C:4](=[CH:5][CH:6]=1)[C:3](=[O:19])[C:2]([OH:1])([C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH3:27])[CH3:28])=[CH:22][C:21]=1[O:29][CH3:30])[C:10]2=[O:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 71477131N-(2-Hydroxy-2-(4-isopropyl-2-methoxyphenyl)-5-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Product 1

HCID 71477133N-(5-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamideYield 98.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-5-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide (0.10 g, 0.24 mmol) was completely dissolved in anhydrous ethanol (3 ml). This solution was added with iron (0.098 g), conc. HCl (0.05 ml) and water (0.3 ml). The reaction mixture was heated for 2 hrs under reflux. After filtration at high temperature to remove iron, the filtrate was concentrated in a vacuum and purified using column chromatography (ethylacetate 100%) to afford the title compound (90 mg, 98%).

Workup

  1. temperatureThe reaction mixture was heated for 2 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-96472b29eea344aabaea3251405c53d3
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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