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

HRID 907176Notes

Reaction equation

HRID 907176 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, was suspended in acetic acid (620 μL) at 0° C. Nitric acid (4.25M in AcOH) was added. This was stirred at room temperature for 2 hours. The reaction mixture was then partitioned between CH2Cl2 and H2O. The organic layer was washed with aqueous NaHCO3, and then was dried and concentrated. Purification by silica gel chromatography (6/4, CH2Cl2/hexanes), followed by ether trituration, yielded 1-ethyl-2-iodo-6-methoxy-5-nitro-1H-indole-3-carbonitrile (16 mg, 29%) as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-10d79f1d62cc49109014fdb730afd386
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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