Hydrochloric Acid → HCID 86717352, compound

HRID 527156Notes

Reaction equation

HRID 527156 reaction equation
Cl.O.[C:3]([O:11][C:12]1[CH:17]=[C:16]([CH:18]([CH3:20])[CH3:19])[CH:15]=[CH:14][C:13]=1[C:21]1([NH:35][C:36](=[O:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[N+:31]([O-])=O)[C:22]1=[O:34])(=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>C(O)C.[Fe]>[C:3]([O:11][C:12]1[CH:17]=[C:16]([CH:18]([CH3:19])[CH3:20])[CH:15]=[CH:14][C:13]=1[C:21]1([NH:35][C:36](=[O:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][C:27]=2[NH2:31])[C:22]1=[O:34])(=[O:10])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86717353HCID 86717353, compound

Product 1

HCID 86717352HCID 86717352, compoundYield 37.4%

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 2-(2-heptanamido-4nitro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-5-isopropylphenyl heptanoate (60 mg, 0.10 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=1:6 to 1:4) to afford the title compound (20 mg, 36%).

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=1:6 to 1:4)

Sources & evidence

ORD record
ord-1e2f754017c240b59400c6c4ca31e878
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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