2-Oxobutanoic Acid → HCID 12979375, compound

HRID 2097174Notes

Reaction equation

HRID 2097174 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-5ae9f0e1b1de499bb7ac2c779fb4df43
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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