Hydrochloric Acid → HCID 71478174, compound

HRID 527170Notes

Reaction equation

HRID 527170 reaction equation
[CH2:1]([NH:3][C:4](=[O:33])[O:5][C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[C:15]1([NH:29][C:30](=[O:32])[CH3:31])[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:25]([O-])=O)[C:16]1=[O:28])[CH3:2].Cl>C(O)C.O.[Fe]>[CH2:1]([NH:3][C:4](=[O:33])[O:5][C:6]1[CH:11]=[C:10]([CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[C:15]1([NH:29][C:30](=[O:32])[CH3:31])[C:23](=[O:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[NH2:25])[C:16]1=[O:28])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86717359HCID 86717359, compound

Product 1

HCID 71478174HCID 71478174, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(2-acetamido-4-nitro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-5-isopropylphenyl ethylcarbamate (0.27 g, 0.59 mmol) was dissolved in Ethanol (10 ml) and water (1 ml). This solution was added with iron (0.24 g, 4.3 mmol) and conc. HCl (0.03 ml). The reaction mixture was heated for 2 hrs under reflux. After filtrating and washing with MeOH, the remainder was concentrated in a vacuum and purified using column chromatography (ethylacetate:hexane=1:1) to afford the title compound (90 mg, 36%).

Workup

  1. temperatureThe reaction mixture was heated for 2 hrs
  2. temperatureunder reflux
  3. filtrationAfter filtrating
  4. washwashing with MeOH
  5. concentrationthe remainder was concentrated in a vacuum
  6. custompurified

Sources & evidence

ORD record
ord-d11ae0dc848a49c2b934fee417e6f169
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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