HCID 131736189, compound → HCID 90102981, compound

HRID 1052534Notes

Reaction equation

HRID 1052534 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[C:4]([N+:19]([O-])=O)[CH:3]=1>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:19])[C:5]2[CH:6]=[CH:7][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])[C:9]=2[CH:10]=1

Participants

4

Reactant 1

HCID 131736189HCID 131736189, compound

Product 1

HCID 90102981HCID 90102981, compoundYield 110.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

6-Chloro-4-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole (1.82 g, 5.35 mmol) was treated with iron powder (1.49 g, 27 mmol) in acetic acid (80 ml) and stirred at room temperature. After 1 h the crude was filtered over Celite and the solvent was removed in vacuum. A mixture of a solution of sodium bicarbonate 4% and ethyl acetate was added and the resulting mixture was filtered over Celite. The organic phase was washed with water and brine, dried over magnesium sulphate and the solvent was removed to give 1.76 g (93% yield) of the title compound as a dark solid, that was used in the next step without further purification. Purity 85%.

Workup

  1. filtrationAfter 1 h the crude was filtered over Celite
  2. customthe solvent was removed in vacuum
  3. additionA mixture of a solution of sodium bicarbonate 4% and ethyl acetate
  4. additionwas added
  5. filtrationthe resulting mixture was filtered over Celite
  6. washThe organic phase was washed with water and brine
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent was removed

Sources & evidence

ORD record
ord-340b70734ea5442e8eff638ad56016a7
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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