5-Benzyloxyindole → 5-benzyloxy-3-(2-nitro-propyl)-1H-indole

HRID 6749

Reaction equation

HRID 6749 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:18]([C:21]([CH3:23])=[CH2:22])([O-:20])=[O:19]>C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[CH2:22][CH:21]([N+:18]([O-:20])=[O:19])[CH3:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 146245-BenzyloxyindoleHCID 784862-Nitro-1-propene

Product 1

HCID 140831715-benzyloxy-3-(2-nitro-propyl)-1H-indole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred 0.5 M benzene solution of 5-benzyloxy-1H-indole (6 mL) was added 2-nitro-propene (5.2 mL of the 10% benzene solution). The reaction was heated at reflux under a nitrogen atmosphere overnight. The volatiles were removed and residue was purified by silica gel chromatography (20% EtOAc/hexanes) to afford 5-benzyloxy-3-(2-nitro-propyl)-1H-indole (550 mg).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere overnight
  3. customThe volatiles were removed
  4. customresidue was purified by silica gel chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-acc4cf61188540a5b8199811016a6ac9
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Linked notes

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