2-Oxobutanoic Acid → HCID 12979375, compound

HRID 1362426Notes

Reaction equation

HRID 1362426 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7]N.O=[C:11]([CH2:15][CH3:16])[C:12]([OH:14])=[O:13].[CH2:17](O)[CH3:18]>>[CH3:16][C:15]1[C:3]2[C:2](=[C:1]([CH3:9])[CH:6]=[CH:5][CH:4]=2)[NH:7][C:11]=1[C:12]([O:14][CH2:17][CH3:18])=[O:13]

Participants

4

Reactant 3

HCID 582-Oxobutanoic AcidHCID 702Ethanol2×HCID 68256o-Tolylhydrazine

Product 1

HCID 12979375HCID 12979375, compoundYield 27%

Conditions

Temperature
50 °C

Procedure

A suspension of 1-o-tolylhydrazine (3.8 g, 30.9 mmol) in ethanol was warmed to 50° C. A solution of α-ketobutyric acid (3.16 g, 30.9 mmol) in ethanol was added and the mixture stirred at rt overnight. Hydrogen chloride was bubbled through the solution for 30 min and the mixture heated at reflux for 2 h then evaporated in vacuo. The crude reaction was chromatographed over silica gel eluting with ethyl acetate/hexane (5%) to afford the title compound (1.84 g, 27%). 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 7.50 (d, J=7.8 Hz, 1H), 7.09 (d, J=6.9 Hz, 1H), 7.03 (t, J=7.6 Hz, 1H), 4.41 (q, J=7.1 Hz, 2H), 2.59 (s, 3H), 2.48 (s, 3H), 1.44 (t, J=7.2 Hz, 3H).

Workup

  1. customHydrogen chloride was bubbled through the solution for 30 min
  2. temperaturethe mixture heated
  3. temperatureat reflux for 2 h
  4. customthen evaporated in vacuo
  5. customThe crude reaction
  6. customwas chromatographed over silica gel eluting with ethyl acetate/hexane (5%)

Sources & evidence

ORD record
ord-293a50948ce1460b9b58ad17aae28cf1
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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