Acetic Acid → Indole

HRID 746820

Reaction equation

HRID 746820 reaction equation
Cl.FC(F)(F)O[C:5]1[CH:10]=[CH:9][C:8]([NH:11]N)=[CH:7][CH:6]=1.[C:15](O)(=O)[CH3:16]>>[NH:11]1[C:8]2[C:7](=[CH:6][CH:5]=[CH:10][CH:9]=2)[CH:16]=[CH:15]1

Participants

3

Reactant 2

HCID 176Acetic Acid2×HCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 798Indole

Procedure

Ketone 2 (3.65 gr, 17 mmol) and 4-trifluoromethoxy phenylhydrazine hydrochloride (4.66 gr, 20.4 mmol) were stirred at reflux in acetic acid (0.25M) for 1 h under nitrogen atmosphere. The reaction was cooled to room temperature the acetic acid was removed under reduced pressure and the residue was diluted with ether and washed with water (1×) and brine (1×). The ether layer was dried with magnesium sulfate, filter and evaporated to afford 3 as a yellow oil after column chromatography (hexanes/ethyl acetate, 4:1); 1H-NMR (CDCl3, 500 MHz) δ 7.79 (br s, 1H), 7.25 (d, 1H), 7.17 (s, 1H), 7.14 (t, 1H), 7.03 (dd, 1H), 6.58 (dd, 1H), 6.50 (dd, 1H), 6.44 (t, 1H), 4.95 (br s, 1H), 2.33 (s, 1H).

Workup

  1. customwas removed under reduced pressure
  2. additionthe residue was diluted with ether
  3. washwashed with water (1×) and brine (1×)
  4. dry with materialThe ether layer was dried with magnesium sulfate
  5. filtrationfilter
  6. customevaporated

Sources & evidence

ORD record
ord-3aff1961992c4ab5bfbae30e02ed3675
Source dataset
uspto-grants-2008_07
Patent number
US07393960B2

Linked notes

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