Hydrazine → HCID 22314380, compound

HRID 966057Notes

Reaction equation

HRID 966057 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:13]([O-])=O)[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].NN>[Ni].CO>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 9321HydrazineHCID 20900Indole, 3-acetyl-5-nitro-

Product 1

HCID 22314380HCID 22314380, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3-acetyl-5-nitroindole (3.0 g, 14.7 mmol) and Raney Nickel (3.0 g) in methanol is treated dropwise with hydrazine (0.7 g, 21.9 mmol) at 0° C., stirred under N2 for 1 h and filtered. The filtrate is concentrated in vacuo to afford the title product as an oil, 2.5 g (99% yield) identified by NMR and mass spectral analyses.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-ff282b7cd89b480790c0b7011fe70c52
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

Loading…