4-Nitrobenzaldehyde → 2-ethyl-3-(4-nitrobenzyl)-1H-indole

HRID 589354Notes

Reaction equation

HRID 589354 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[CH2:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:16].[N+:26]([C:29]1[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=1)([O-:28])=[O:27].[OH-].[Na+].[Cl-].[Na+]>ClCCl>[CH2:15]([C:17]1[NH:18][C:19]2[C:24]([C:25]=1[CH2:33][C:32]1[CH:35]=[CH:36][C:29]([N+:26]([O-:28])=[O:27])=[CH:30][CH:31]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH3:16]

Participants

8

Reactant 6

HCID 5414-NitrobenzaldehydeHCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 38016182-ethyl-1H-indole

Product 1

HCID 895902792-ethyl-3-(4-nitrobenzyl)-1H-indoleYield 41.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In an ice water bath, trifluoroacetic acid (4.4 g, 38.6 mmol), triethylsilane (9.02 g, 77.6 mmol), dichloromethane 15 mL were added into a reaction vessel. After stirring for 5 min, a dichloromethane solution dissolving 2-ethyl-1H-indole (3.74 g, 25.8 mmol) and p-nitro benzaldehyde (4.29 g, 28.4 mmol) was added dropwise slowly into the reaction vessel. After completion of dropwise addition it was reacted maintaining this temperature for 1 h, adjusted to pH=8-9 with 2 M solution of sodium hydroxide. An aqueous solution of sodium chloride was added, and extracted with dichloromethane. The extract was dried over anhydrous sodium sulfate, concentrated to dryness to obtain a red brown solid, washed with a small amount of diethyl ether to obtain a yellow powdered solid 3 g, at a yield of 41.5%.

Workup

  1. additionwas added dropwise slowly into the reaction vessel
  2. additionAfter completion of dropwise addition it
  3. customwas reacted
  4. temperaturemaintaining this temperature for 1 h
  5. extractionextracted with dichloromethane
  6. dry with materialThe extract was dried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customto obtain a red brown solid
  9. washwashed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-feadee64bba44a5d9a9e3fba348c6248
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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