Water → HCID 68487222, compound

HRID 1874990Notes

Reaction equation

HRID 1874990 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][CH2:18][CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12].O.CCOC(C)=O>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])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 7516PhenylhydrazineHCID 8857Ethyl AcetateHCID 10236026ethyl 2-oxohexanoate

Product 1

HCID 68487222HCID 68487222, compoundYield 58.1%

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-oxohexanoate (1.0 g, 6.33 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 for 18 h. Water (25 mL) and EtOAc (25 mL) were added and the layers separated. The aqueous layer was extracted with EtOAc (2×25 mL), the organic layers combined, dried over sodium sulfate, filtered and concentrated. Trituration of the crude material (9:1 hexanes/EtOAc) afforded ethyl 3-propyl-1H-indole-2-carboxylate (0.850 g, 58%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.46 (s, 1H) 7.65 (d, 1H) 7.40 (d, 1H) 7.25 (d, 1H) 7.04 (t, 1H) 4.33 (q, 2H) 3.02 (t, 2H) 1.56-1.67 (m, 2H) 1.35 (t, 3H) 0.91 (t, 3H). MS: m/z 232.0 (M+1).

Workup

  1. customa reflux condenser attached
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with EtOAc (2×25 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-117663f8d7cc41dca3ace827e27b59d4
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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