Water → HCID 12562460, compound

HRID 2185963Notes

Reaction equation

HRID 2185963 reaction equation
[Li][CH:2]([CH2:4][CH3:5])[CH3:3].[C:6](#[N:9])[CH2:7][CH3:8].[OH2:10]>C1COCC1>[CH2:4]([C:2]1[NH:9][C:6](=[O:10])[C:7]2[C:5]([CH:3]=1)=[CH:4][CH:2]=[CH:3][CH:8]=2)[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 7854PropionitrileHCID 178418400CID 53628100

Product 1

HCID 12562460HCID 12562460, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

O-Toluic acid (2.0 g. 14.7 mmol) in THF (75 ml) was cooled to −78° and sec—BuLi (22.5 ml) added slowly. The resulting red solution was warmed to 0° for 30 min then cooled to −78°. Propionitrile (1.05 ml) in THF (10 ml) was added. the solution allowed to warm and stirred to RT for 16 h. Water (100 ml) was added and the product extracted into EtOAc (100 ml), washed with dilute HCl solution, water, brine, dried ((Na2SO4), and concentrated in vacuo. The crude product was purified by chromatography (SiO2; 1-5% DCM/MeOH) ) to give the title compound (1.12 g, 44%) as a white solid. δH (CDCl3) 8.37 (1H, d, J 8.0 Hz). 7.63 (1H, t, J 8.0 Hz), 7.48 (1H, d, J 8.0 Hz). 7.42 (1H, t, J 8.0 Hz), 6.33 (1H, s), 2.67 (2H, q, J 7.6 Hz), 1.33 (3H, t, J 7.6 Hz). m/z (ES+, 70V) 174 (MH+).

Workup

  1. temperatureThe resulting red solution was warmed to 0° for 30 min
  2. temperaturethen cooled to −78°
  3. temperatureto warm
  4. extractionthe product extracted into EtOAc (100 ml)
  5. washwashed with dilute HCl solution, water, brine
  6. dry with materialdried ((Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography (SiO2; 1-5% DCM/MeOH) )

Sources & evidence

ORD record
ord-eaa9caf06b4c4841b039b33f9c667ba8
Source dataset
uspto-grants-2002_06
Patent number
US06403608B1

Reaction notes

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