HCID 21071457, compound → HCID 21071583, compound

HRID 1371909Notes

Reaction equation

HRID 1371909 reaction equation
[N+:1]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH:7]=1)([O-])=O>O=[Pt]=O.CO>[CH3:18][O:17][C:15]([C:12]1[CH:13]=[C:14]2[C:9]([NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][NH2:1])=[CH:10][CH:11]=1)=[O:16]

Participants

4

Reactant 1

HCID 21071457HCID 21071457, compound

Product 1

HCID 21071583HCID 21071583, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Combine 3-(2-nitroethyl)-5-methoxycarbonyl-1H-indole (280 mg, 1.1 mmol), PtO2 (200 mg) and 15 mL MeOH and hydrogenate at atmospheric pressure overnight. Filter reaction mixture through a pad of celite, concentrate the filtrate, and chromatograph on silica gel eluting with 5% MeOH in CHCl3 mixed with conc. NH4OH to give the title compound as an oil: ISMS 219 (M+1); 1H NMR (CDCl3) 9.01 (s, 1H), 8.36 (s, 1H), 7.88–7.85 (m, 1H), 7.32–7.24 (m, 1H), 7.05 (s, 1H), 3.91 (s, 3H), 3.05–3.01 (m, 2H), 2.93–2.89 (m, 2H), 1.22 (bs, 2H).

Workup

  1. customhydrogenate at atmospheric pressure overnight
  2. filtrationFilter
  3. customreaction mixture through a pad of celite
  4. concentrationconcentrate the filtrate, and chromatograph on silica gel eluting with 5% MeOH in CHCl3
  5. additionmixed with conc. NH4OH

Sources & evidence

ORD record
ord-249d404b0c9148239903025fee119232
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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