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

HRID 589336Notes

Reaction equation

HRID 589336 reaction equation
FC(F)(F)C(O)=O.C([SiH](CC)CC)C.[CH3:15][C:16]1[NH:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.[N+:25]([C:28]1[CH:35]=[CH:34][C:31]([CH:32]=O)=[CH:30][CH:29]=1)([O-:27])=[O:26].[OH-].[Na+].[Cl-].[Na+]>ClCCl>[CH3:15][C:16]1[NH:17][C:18]2[C:23]([C:24]=1[CH2:32][C:31]1[CH:34]=[CH:35][C:28]([N+:25]([O-:27])=[O:26])=[CH:29][CH:30]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2

Participants

8

Reactant 6

HCID 5414-NitrobenzaldehydeHCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 72242-MethylindoleHCID 12052TriethylsilaneHCID 14798Sodium Hydroxide

Product 1

HCID 861743212-Methyl-3-(4-nitrobenzyl)-1H-indoleYield 40.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In an ice water bath, into a reaction vessel were added trifluoroacetic acid (6.824 g, 60 mmol), triethylsilane (13.9 g, 120 mmol), dichloromethane 20 mL. After stirring for 5 min, a dichloromethane solution dissolving 2-methyl-1H-indole (5.24 g, 40 mmol) and p-nitro benzaldehyde (6.67 g, 44 mmol) was added dropwise slowly into the reaction vessel. After completion of dropwise addition, it was reacted maintaining this temperature for 1 h. It was 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, and washed with diethyl ether to obtain a yellow powdered solid 4.3 g, at a yield of 40.3%.

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 diethyl ether

Sources & evidence

ORD record
ord-4d5a914fac4b48c09de342af949712d3
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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