Hydrochloric Acid → HCID 86717357, compound

HRID 527168Notes

Reaction equation

HRID 527168 reaction equation
[CH3:1][N:2]([CH3:33])[C:3](=[O:32])[O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[C:14]1([NH:28][C:29](=[O:31])[CH3:30])[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[N+:24]([O-])=O)[C:15]1=[O:27].Cl>C(O)C.O.[Fe]>[CH3:33][N:2]([CH3:1])[C:3](=[O:32])[O:4][C:5]1[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[C:14]1([NH:28][C:29](=[O:31])[CH3:30])[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[NH2:24])[C:15]1=[O:27]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86717358HCID 86717358, compound

Product 1

HCID 86717357HCID 86717357, compoundYield 53.1%

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 dimethylcarbamate (0.20 g, 0.4 mmol) was dissolved in anhydrous ethanol (10 ml) and water (1 ml). This solution was added with iron (0.18 g, 3.2 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=1:2) to afford the title compound (90 mg, 50%).

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-4ed02977a94948e591f06bdaaa3a4262
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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