Hydrochloric Acid → HCID 86717350, compound

HRID 527155Notes

Reaction equation

HRID 527155 reaction equation
Cl.O.[C:3]([O:10][C:11]1[CH:16]=[C:15]([CH:17]([CH3:19])[CH3:18])[CH:14]=[CH:13][C:12]=1[C:20]1([NH:34][C:35](=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[N+:30]([O-])=O)[C:21]1=[O:33])(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)C.[Fe]>[C:3]([O:10][C:11]1[CH:16]=[C:15]([CH:17]([CH3:18])[CH3:19])[CH:14]=[CH:13][C:12]=1[C:20]1([NH:34][C:35](=[O:41])[CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][C:26]=2[NH2:30])[C:21]1=[O:33])(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86717351HCID 86717351, compound

Product 1

HCID 86717350HCID 86717350, compoundYield 59.2%

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-hexanamido-4-nitro-1,3-dioxo-2,3-dihydro-1H-inden-2-yl)-5-isopropylphenyl hexanoate (40 mg, 0.07 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 (21 mg, 57%).

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-70a645d8be834e52b539cf123e78139c
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

Loading…