Hydrochloric Acid → HCID 71477752, compound

HRID 527157Notes

Reaction equation

HRID 527157 reaction equation
Cl.O.[C:3]([O:7][C:8]1[CH:13]=[C:12]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[C:17]1([NH:31][C:32](=[O:35])[CH2:33][CH3:34])[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[N+:27]([O-])=O)[C:18]1=[O:30])(=[O:6])[CH2:4][CH3:5]>C(O)C.[Fe]>[C:3]([O:7][C:8]1[CH:13]=[C:12]([CH:14]([CH3:15])[CH3:16])[CH:11]=[CH:10][C:9]=1[C:17]1([NH:31][C:32](=[O:35])[CH2:33][CH3:34])[C:25](=[O:26])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[NH2:27])[C:18]1=[O:30])(=[O:6])[CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86717354HCID 86717354, compound

Product 1

HCID 71477752HCID 71477752, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (0.03 g, 0.5 mmol), conc. HCl (0.05 ml), and water (0.5 ml) were added in that order to a solution of 5-isopropyl-2-(4-nitro-1,3-dioxo-2-propionamido-2,3-dihydro-1H-inden-2-yl)phenyl propionate (40 mg, 0.08 mmol) in ethanol (5 ml). The reaction mixture was heated for 1 hrs under reflux. The reaction mixture was hot filtered off, the filtrate was concentrated in a vacuum and purified by column chromatography (ethylacetate:hexane=1:4 to 1:2) to afford the title compound (28 mg, 75%).

Workup

  1. temperatureThe reaction mixture was heated for 1 hrs
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was hot filtered off
  4. concentrationthe filtrate was concentrated in a vacuum
  5. custompurified by column chromatography (ethylacetate:hexane=1:4 to 1:2)

Sources & evidence

ORD record
ord-074eda46a3e2483ea5b0e6f177e3bde1
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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