Nitric Acid → 1-ethyl-2-iodo-6-methoxy-5-nitro-1H-indole-3-carbonitrile

HRID 506076Notes

Reaction equation

HRID 506076 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[I:16])[CH3:2].[N+:17]([O-])([OH:19])=[O:18]>C(O)(=O)C>[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:17]([O-:19])=[O:18])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1[I:16])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 594256441-ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 594253901-ethyl-2-iodo-6-methoxy-5-nitro-1H-indole-3-carbonitrileYield 29%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-Ethyl-2-iodo-6-methoxy-1H-indole-3-carbonitrile (50 mg, 0.15 mmol), prepared as in example 1Ga, Step A, is suspended in acetic acid (620 μL) at 0° C. Nitric acid (4.25M in AcOH) is added. This is stirred at room temperature for 2 hours. The reaction mixture is then partitioned between CH2Cl2 and H2O. The organic layer is washed with aqueous NaHCO3, and then is dried and concentrated. Purification by silica gel chromatography (6/4, CH2Cl2/hexanes), followed by ether trituration, yields 1-ethyl-2-iodo-6-methoxy-5-nitro-1H-indole-3-carbonitrile (16 mg, 29%) as a yellow solid.

Workup

  1. customThe reaction mixture is then partitioned between CH2Cl2 and H2O
  2. washThe organic layer is washed with aqueous NaHCO3
  3. customis dried
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (6/4, CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-ba0f64c715f341b39f569165165a88d2
Source dataset
uspto-grants-2010_08
Patent number
US07781478B2

Reaction notes

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