3-Methyl-2-butanone → HCID 71736007, compound

HRID 403601Notes

Reaction equation

HRID 403601 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9]N)[CH:5]=[C:6]([I:8])[CH:7]=1.[CH3:11][CH:12]([CH3:16])[C:13](=O)[CH3:14]>C(O)(=O)C>[I:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]2[C:3]=1[C:12]([CH3:16])([CH3:11])[C:13]([CH3:14])=[N:9]2

Participants

4

Reactant 2

HCID 112513-Methyl-2-butanoneHCID 86695330HCID 86695330, compound

Product 1

HCID 71736007HCID 71736007, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2 g of 3,5-diiodophenylhydrazine (5.5 mmol), and 1 mL (9.3 mmol) of 3-methyl-2-butanone were refluxed in 15 mL of acetic acid for 20 hours. The acetic acid was evaporated and the residue was dissolved in ether. Insoluble precipitate was filtered off, and the etheric solution was washed with aqueous solutions of NaHCO3, followed by Na2S2O3 and water. The organic layer was dried with CaCl2 and ether was removed under reduced pressure by a rotary evaporator to give 1.4 g of 4,6-diiodo-2,3,3-trimethyl-3H-indole. 1H-NMR (200 MHz, DMSO-d6), δ, ppm: 7.92 (1H, d, 1.1 Hz, arom.), 7.79 (1H, d, 1.1 Hz, arom.), 2.22 (3H, s, 2-CH3), 1.32 (6H, s, C(CH3)2).

Workup

  1. customThe acetic acid was evaporated
  2. dissolutionthe residue was dissolved in ether
  3. filtrationInsoluble precipitate was filtered off
  4. washthe etheric solution was washed with aqueous solutions of NaHCO3
  5. dry with materialThe organic layer was dried with CaCl2 and ether
  6. customwas removed under reduced pressure by a rotary evaporator

Sources & evidence

ORD record
ord-6b53ca98b2d74f7c8ef71630fa3433ee
Source dataset
uspto-grants-2014_06
Patent number
US08748446B2

Reaction notes

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