Hydrochloric Acid → HCID 71476021, compound

HRID 527173Notes

Reaction equation

HRID 527173 reaction equation
[OH:1][C:2]1([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:17]=2[NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[C:3]1=[O:15].Cl>C(O)C.O.[Fe]>[NH2:12][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[C:10](=[O:11])[C:2]([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:17]=1[NH:26][C:27](=[O:31])[CH:28]([CH3:30])[CH3:29])([OH:1])[C:3]2=[O:15]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86717360HCID 86717360, compound

Product 1

HCID 71476021HCID 71476021, compoundYield 12.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

N-[2-(2-hydroxy-4-nitro-1,3-dioxo-indan-2-yl)-4,5-dimethoxy-phenyl]-isobutyramide (150 mg, 0.35 mmol) was dissolved in ethanol (3 ml) and water (0.3 ml). This solution was added with iron (Fe) (0.14 g, 2.55 mmol) and conc. HCl (0.03 ml), followed by heating for 3 hrs under reflux. The reaction mixture was filtrated with MeOH washing via celite pad, and the filtrate was concentrated in a vaccume. The concentrated organic layer was purified using column chromatography (ethylacetate:hexane=1:4) to afford the title compound (17 mg, 12%).

Workup

  1. temperatureby heating for 3 hrs
  2. temperatureunder reflux
  3. filtrationThe reaction mixture was filtrated with MeOH washing via celite pad
  4. concentrationthe filtrate was concentrated in a vaccume
  5. customThe concentrated organic layer was purified

Sources & evidence

ORD record
ord-c15e2435e0a341cba6d279c1d09fd95f
Source dataset
uspto-grants-2016_05
Patent number
US09346749B2

Reaction notes

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