Acetic Anhydride → HCID 44581689, compound

HRID 1775428Notes

Reaction equation

HRID 1775428 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]2[CH2:17][CH2:18][N+:19]([O-])=O.[C:22](OC(=O)C)(=[O:24])[CH3:23].[H][H]>[Ni].O1CCCC1>[C:22]([NH:19][CH2:18][CH2:17][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][C:7]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 118071533HCID 118071533, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 44581689HCID 44581689, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixed solution of ethyl 5-methoxy-3-(2-nitroethyl)-1H-indole-2-carboxylate (500 mg), tetrahydrofuran (40.0 mL), and acetic anhydride (2.00 mL) was pumped through Raney nickel cartridge, using H-cube (registered trademark) (ThalesNano Inc.) apparatus (catalyst cartridge: CatCart (registered trademark) (ThalesNano Inc.) hydrogen pressure: 60 bar, reaction temperature: 60° C., flow rate: 1 mL/s, solution concentration: 0.05 M). The obtained mixture was concentrated under reduced pressure and the obtained residue was washed with a mixed solvent of hexane:ethyl acetate=2:1 to obtain ethyl 3-(2-acetamidoethyl)-5-methoxy-1H-indole-2-carboxylate (450 mg) as a white solid.

Workup

  1. concentrationThe obtained mixture was concentrated under reduced pressure
  2. washthe obtained residue was washed with a mixed solvent of hexane

Sources & evidence

ORD record
ord-9ef0ec02a93e4a3c8874a67887da094b
Source dataset
uspto-grants-2016_02
Patent number
US09260445B2

Reaction notes

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