Phenylhydrazine → HCID 15942915, compound

HRID 1874989Notes

Reaction equation

HRID 1874989 reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:10]([CH2:16][CH2:17][CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C>[CH2:17]([C:16]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[NH:7][C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH3:18]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 123521Ethyl 2-oxovalerate

Product 1

HCID 15942915HCID 15942915, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of phenylhydrazine (1.0 g, 6.92 mmol) in absolute ethanol (50 mL) was placed in an oil bath at 60° C. and a reflux condenser attached. Ethyl 2-oxopentanoate (1.0 g, 6.94 mmol) (prepared according to Singh, J; Kissick, T. P.; Mueller, R. H. Organic Preparations and Procedures International (1989), 21(4), 501-4.) was added dropwise. The reaction mixture was heated to reflux and stirred overnight. The solution was cooled to RT and the solvent concentrated. Purification was accomplished by column chromatography (hexanes:EtOAc) to afford ethyl 3-ethyl-1H-indole-2-carboxylate (0.625 g, 41%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.45 (s, 1H) 7.66 (d, 1H) 7.41 (d, 1H) 7.25 (t, 1H) 7.05 (t, 1H) 4.34 (q, 2H) 3.05 (q, 2H) 1.35 (t, 3H) 1.19 (t, 3H). MS: m/z 218.0 (M+1).

Workup

  1. customa reflux condenser attached
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. concentrationthe solvent concentrated
  5. customPurification

Sources & evidence

ORD record
ord-493a6a6381f447899911db5bc4967c1e
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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