HCID 68597147, compound → HCID 46195426, compound

HRID 1965490Notes

Reaction equation

HRID 1965490 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][CH2:13][O:14][C:7]3=[CH:6][C:5]=2[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N+:25]([O-])=O)([C:15]([O:17]C)=O)[C:3]1=[O:28]>[Pd].CO>[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][CH2:13][O:14][C:7]3=[CH:6][C:5]=2[C:4]2([C:19]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:25][C:15]2=[O:17])[C:3]1=[O:28]

Participants

4

Reactant 1

HCID 68597147HCID 68597147, compound

Product 1

HCID 46195426HCID 46195426, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of methyl 6-methyl-8-(2-nitrophenyl)-7-oxo-2,3,7,8-tetrahydro-6H-[1,4]dioxino[2,3-f]indole-8-carboxylate (0.21 g, 0.54 mmol) and 10% w/w palladium on carbon (0.1 g) in methanol (20 mL) was hydrogenated at 1 atm and at ambient temperature for 20 h. The mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated in vacuo. The residue was subjected to column chromatography to afford 6-methyl-2,3-dihydrospiro[1,4-dioxino[2,3-f]indole-8,3′-indole]-2′,7(1H,6H)-dione (0.07 g, 40%): MS (ES+) m/z 323.0 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6f56b82fcd89418bade4886b332796fe
Source dataset
uspto-grants-2013_04
Patent number
US08415370B2

Reaction notes

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