Hydrochloric Acid → N-(7-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

HRID 527132Notes

Reaction equation

HRID 527132 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](=[C:5]([N+:16]([O-])=O)[CH:6]=[CH:7][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:5]1[CH:6]=[CH:7][C:8]([NH:12][C:13](=[O:15])[CH3:14])=[C:9]2[C:4]=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 71476974N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-nitro-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamide

Product 1

HCID 71477132N-(7-Amino-2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-1,3-dioxo-2,3-dihydro-1H-inden-4-yl)acetamideYield 71%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

N-(2-hydroxy-2-(4-isopropyl-2-methoxyphenyl)-7-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:hexane=1:2) to afford the title compound (65 mg, 71%).

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-d5a55c45de464977b7452fcc307801d6
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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